JPH11255729A - Production of alpha-aminonitrile - Google Patents

Abstract

PROBLEM TO BE SOLVED: To readily obtain an α-aminonitrile by suing inexpensive raw materials, by reacting a specific tertiary amine with a cyanide in the presence of a transition metal catalyst and hydrogen peroxide. SOLUTION: (A) A tertiary amine of formula I [R<1> is a (substituted) phenyl; R<2> is an alkyl or a (substituted) phenyl; R<3> is H, an alkyl or a (substituted) phenyl; R<2> and R<3> are bonded to form a nitrogen-containing ring] (e.g. N- dimethylaniline) is reacted with (B) 1-10 times mols based in the component A of a cyanide such as an alkali metal cyanide (e.g. sodium cyanide), hydrogen cyanide or the like in the presence of (C) >=0.01 mol.%, based on the component A and calculated as anhydride, of a transition metal catalyst such as a ruthenium halide, an iron halide, a manganese halide (e.g. ruthenium and (D) 1-100 mols based on the component A of hydrogen peroxide to give an α-aminonitrile of formula II.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

[0001] The present invention relates to a method for producing α-aminonitrile.

[0002]

2. Description of the Related Art α-aminonitrile is useful as an intermediate for pharmaceuticals, agricultural chemicals, etc., for example, by a method utilizing anodic oxidation [J. Am. Chem. Soc., 91, 4181 (1969).
], Photoreaction method [Tetrahedron Lett., 31,
4735 (1990)], a method using chlorine dioxide [J.
Am. Chem. Soc., 110, 4829 (1988)], a method using 1-cyano-3- (1H) -1,2-benziodoxol [Tetrahedron Lett., 36, 7975 (199).
5)], a method using cyanogen iodide [Tetrahedron L
ett., 38, 6119 (1997)]. However, these methods have problems such as the necessity of using a special reaction apparatus and the use of a special reaction reagent which is difficult to obtain industrially, and cannot be said to be an industrial production method. On the other hand, the present inventors have already found an industrial method for producing α-aminonitrile by reacting a tertiary amine with trimethylsilyl cyanide in the presence of ruthenium chloride and peracetic acid (The 70th Spring Year of the Chemical Society of Japan). Proceedings of the Society 3J247), this method requires further improvement as an industrial production method from the viewpoint that relatively expensive trimethylsilyl cyanide and peracetic acid are used and that there are many by-products.

[0003]

SUMMARY OF THE INVENTION
The present inventors further studied an industrial production method of α-aminonitrile, and found that α-aminonitrile was produced from tertiary amines using inexpensive cyanide and inexpensive and easy-to-handle hydrogen peroxide.
The present inventors have found that aminonitrile can be easily produced, and have reached the present invention.

[0004]

According to the present invention, there is provided a compound represented by the general formula (1): (Wherein, R ¹ represents an optionally substituted phenyl group, R ² represents an alkyl group or an optionally substituted phenyl group, and R ³ represents a hydrogen atom, an alkyl group or an optionally substituted And R ² and R ³ may combine to form a nitrogen-containing ring) with a cyanide in the presence of a transition metal catalyst and hydrogen peroxide. General formula (2) characterized by reacting (Wherein R ¹ , R ² and R ³ have the same meanings as described above).

[0005]

BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in detail. In the compound represented by the general formula (1), examples of the optionally substituted phenyl group for the substituent R ¹ include a phenyl group, a 2-methylphenyl group, a 3-methylphenyl group, and a 4-methylphenyl group. Lower alkyl-substituted phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2-bromophenyl, 3
A halogen-substituted phenyl group such as -bromophenyl group and 4-bromophenyl group; a lower alkoxy-substituted phenyl group such as 2-methoxyphenyl group, 3-methoxyphenyl group and 4-methoxyphenyl group.

Examples of the alkyl group for the substituents R ² and R ³ include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an s-butyl group, a t-butyl group and a pentyl group. , Hexyl group, cyclohexyl group and the like may be substituted as a phenyl group, for example, a phenyl group,
Lower alkyl-substituted phenyl groups such as 2-methylphenyl group, 3-methylphenyl group and 4-methylphenyl group;
Halogen-substituted phenyl groups such as chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, 2-bromophenyl group, 3-bromophenyl group, 4-bromophenyl group, 2-methoxyphenyl group, 3-methoxyphenyl group, And lower alkoxy-substituted phenyl groups such as -methoxyphenyl group. When R ² and R ³ combine to form a nitrogen-containing ring, examples of the ring include piperidine,
Pyrrolidine, azetidine, 1,2,3,4-tetrahydroquinoline, 1,2,3,4-tetrahydroisoquinoline and the like can be mentioned.

Specific examples of the tertiary amine represented by the general formula (1) include, for example, N, N-dimethylaniline, N-methyl-N-ethylaniline, N, N-diethylaniline, N-phenyl-N- Methylaniline, N, N, 4-
Trimethylaniline, N, N-dimethyl-4-chloroaniline, N, N-dimethyl-4-bromoaniline,
N-dimethyl-4-methoxyaniline, N-phenylpiperidine, N- (4-methoxyphenyl) piperidine,
N-phenylazetidine, N-phenyl 1,2,3,4
-Tetrahydroisoquinoline, 6-benzyloxy-N
-Phenyl-7-methoxy-1,2,3,4-tetrahydroisoquinoline and the like.

Examples of the cyanide include alkali metal cyanides such as sodium cyanide and potassium cyanide, and hydrogen cyanide. The amount of the cyanide is usually 1 to 10 with respect to the tertiary amine represented by the general formula (1). The molar ratio is preferably 1 to 5 molar times. Such a cyanide may be used as it is, or may be dissolved in a solvent described later and used as a solution.

As the transition metal catalyst, usually, ruthenium halide, iron halide and manganese halide are used, and ruthenium halide is preferably used. These transition metal catalysts can be used either as anhydrides or hydrates. Examples of the ruthenium halide include ruthenium chloride, ruthenium bromide, ruthenium iodide, and the following general formula (3) (Wherein, X represents a halogen atom, and R ⁴ represents an alkyl group, a cycloalkyl group, or a phenyl group which may be substituted).
In the phosphine compound represented by the general formula (3), X is a chlorine atom, a bromine atom, or an iodine atom, and the alkyl group of R ⁴ is a methyl group, an ethyl group, an n-propyl group, an n-butyl group, or an n-butyl group. A hexyl group or the like, a cycloalkyl group as a cyclohexyl group, a cyclopentyl group or the like, and an optionally substituted phenyl group as a phenyl group, a 2-methylphenyl group, a 3-methylphenyl group,
Examples thereof include a 4-methylphenyl group, a 2-chlorophenyl group, a 3-chlorophenyl group, and a 4-chlorophenyl group. Such phosphinated compounds include, for example, dichlorotris (triphenylphosphine) ruthenium, dichlorotris (tri-n-butylphosphine) ruthenium and the like, which may be commercially available or prepared according to a known method. May be done. Examples of the iron halide include ferric chloride, and examples of the manganese halide include manganese chloride and manganese bromide.

The amount of the transition metal catalyst to be used is usually 0.01 as an anhydride with respect to the tertiary amine represented by the general formula (1).
Mol% or more, preferably 0.1 mol% or more, and the upper limit is not particularly limited, but is usually 20% from an economic viewpoint.
Mol%.

[0011] Hydrogen peroxide is usually used as an aqueous solution,
The concentration is usually 0.1 to 80% by weight, preferably 1 to 6%.
The range is 0% by weight. The amount of the tertiary amine represented by the general formula (1) is usually 1 to 100 times by mole,
Preferably, it is in the range of 1 to 10 times.

The reaction is carried out by mixing a tertiary amine represented by the general formula (1), a transition metal catalyst, hydrogen peroxide, and a cyanide. Hydrogen peroxide is added to the mixture of transition metal catalyst, cyanide.

In such a reaction, a solvent may be used. Examples of the solvent include hydrocarbons, alcohols, and the like.
Halogenated hydrocarbons, esters, ketones, and carboxylic acids may be used alone or in combination of two or more thereof, preferably, a mixed solvent of alcohols and carboxylic acids, and the mixing ratio thereof (alcohols / The carboxylic acid (volume ratio) is usually 0.01 to 100, preferably 0.1 to 10. As hydrocarbons, hexane,
Heptane, toluene, benzene and the like include alcohols such as methanol, ethanol, n-propanol, i
-Propanol, n-butanol, s-butanol, t
-Butanol, n-pentanol, etc., as halogenated hydrocarbons, dichloromethane, 1,2-dichloroethane, chlorobenzene, etc., as esters, ethyl acetate, etc., and as ketones, acetone, 4-methyl. -2-pentanone and the like, carboxylic acids as acetic acid,
Examples thereof include propionic acid, butanoic acid, and pentanoic acid.
The amount of the solvent to be used is not particularly limited, but is usually 1 to 50 times the weight of the tertiary amine represented by the general formula (1). The reaction temperature is usually in the range of -50C to 100C, preferably 0-50C.

After completion of the reaction, the reaction mass is usually made alkaline, and a hydrophobic organic solvent is added, if necessary, to perform an extraction treatment, whereby an organic layer containing α-aminonitrile represented by the general formula (2) is obtained. However, since hydrogen peroxide usually remains in the reaction mass, it is preferable to perform the above treatment after adding an aqueous solution of sodium sulfite to decompose the remaining hydrogen peroxide. From the obtained organic layer containing α-aminonitrile, α-aminonitrile can be taken out by a usual method such as extraction, recrystallization or column chromatography.

Specific examples of the α-aminonitrile thus produced include, for example, N-phenyl-N-methylaminoacetonitrile, N-phenyl-N-ethylaminoacetonitrile, N, N-diphenylaminoacetonitrile, 2- ( N-ethyl-N-phenylamino) propionitrile, N- (4-chlorophenyl) -N-methylaminoacetonitrile, N- (4-bromophenyl)-
N-methylaminoacetonitrile, N- (4-methoxyphenyl) -N-methylaminoacetonitrile, 2-cyano-N-phenylpiperidine, 2-cyano-N- (4
-Methoxyphenyl) piperidine, 1-cyano-N-phenyl-1,2,3,4-tetrahydroisoquinoline,
1-cyano-6-benzyloxy-N-phenyl-7-
Methoxy-1,2,3,4-tetrahydroisoquinoline and the like.

The α-aminonitrile obtained according to the present invention can be easily derived into the corresponding α-amino acid by, for example, hydrolyzing according to a conventional method for hydrolyzing nitrile to carboxylic acid.

[0017]

According to the production method of the present invention, .alpha.-aminonitrile useful as an intermediate for pharmaceuticals and agricultural chemicals can be industrially advantageously produced.

[0018]

EXAMPLES The present invention will be described below in detail with reference to examples, but the present invention is not limited thereto. Example 1 13 mg (0.05 mmol) of ruthenium chloride hydrate and 59 mg (1.20 mmol) of sodium cyanide were placed in a 25 mL-equipped eggplant-shaped flask with a branch volume, and the inside of the reaction vessel was purged with argon. Then, at room temperature, 1.7 mL of a methanol-acetic acid mixed solvent (3/1 by volume) and 121 mg (1.00 mmol) of N, N-dimethylaniline were added. To this mixture, 280 mg of 30% aqueous hydrogen peroxide was added dropwise over 1 hour. After dropping, the mixture was stirred at room temperature for 1 hour,
5 ml of a 5% aqueous sodium sulfite solution was added to decompose the remaining hydrogen peroxide, and a saturated aqueous sodium hydrogen carbonate solution was added to make the reaction mixture alkaline. Extraction was performed once with 10 mL of ethyl acetate and twice with 5 mL, and the obtained extract was washed with saturated saline and dried over sodium sulfate to obtain a solution of N-phenyl-N-methylaminoacetonitrile in ethyl acetate. I got When the solution was analyzed by a gas chromatography internal standard method, the conversion of N, N-dimethylaniline was 99%.
%, Yield of N-phenyl-N-methylaminoacetonitrile was 82% (vs. N, N-dimethylaniline). The yield of N-methyl-N-phenylformamide, a by-product, was 1% (vs. N, N-dimethylaniline).

EXAMPLE 2 13 mg (0.05 mmol) of ruthenium chloride hydrate, 59 mg (1.20 mmol) of sodium cyanide, 4-methoxy-
151 mg of N, N-dimethylaniline (1.00 mmol
1) was added, and the inside of the reaction vessel was replaced with argon. Then, a mixed solvent of methanol and acetic acid (volume ratio: 3/1) 1.7 at room temperature.
mL was added. This mixture is mixed with 30% aqueous hydrogen peroxide 170
mg was added dropwise over 1 hour. After the completion of dropping, 30
After stirring for 5 minutes, 5 ml of a 5% aqueous sodium sulfite solution was added to decompose the remaining hydrogen peroxide, and a saturated aqueous sodium hydrogen carbonate solution was added to make the reaction mixture alkaline. Extraction treatment was performed once with 10 mL of ethyl acetate and twice with 5 mL, and the obtained extract was washed with saturated saline, dried over sodium sulfate, and extracted with N-
A solution of cyanomethyl-N-methyl-4-methoxyaniline in ethyl acetate was obtained. The solution was analyzed by gas chromatography internal standard method to find that 4-methoxy-N,
The conversion of N-dimethylaniline was 91%, and the yield of N-cyanomethyl-N-methyl-4-methoxyaniline was 68%.
% (Vs. 4-methoxy-N, N-dimethylaniline). N- (4-methoxyphenyl)-which is a by-product
The yield of N-methylformamide was 2% (vs. 4-methoxy-N, N-dimethylaniline).

Example 3 13 mg (0.05 mmol) of ruthenium chloride hydrate and 59 mg (1.20 mmol) of sodium cyanide were charged into a 25 mL-equipped eggplant-shaped flask with an inner volume of 25 mL, and the inside of the reaction vessel was purged with argon. Then, at room temperature, 1.7 mL of a methanol-acetic acid mixed solvent (3/1 by volume) and 135 mg (1.00 mmol) of N, N-dimethyl-p-toluidine were added. To this mixture, 280 mg of 30% aqueous hydrogen peroxide was added.
It was dropped over time. After completion of the dropwise addition, the mixture was stirred at room temperature for 30 minutes, and 5 ml of a 5% aqueous sodium sulfite solution was added to decompose the remaining hydrogen peroxide, and a saturated aqueous sodium hydrogen carbonate solution was added to make the reaction mixture alkaline. 5 times once with 10 mL of ethyl acetate
Extraction was performed twice with mL, and the obtained extract was washed with saturated saline and dried over sodium sulfate to obtain a solution of N-cyanomethyl-N-methyl-4-methylaniline in ethyl acetate. When the solution was analyzed by gas chromatography internal standard method, the conversion of N, N-dimethyl-p-toluidine was 95% and the yield of N-cyanomethyl-N-methyl-4-methylaniline was 81% (vs. N, N-dimethyl-p-toluidine). N- by-product
The yield of (4-methylphenyl) -N-methylformamide was 2% (vs. N, N-dimethyl-p-toluidine).

Example 4 13 mg (0.05 mmol) of ruthenium chloride hydrate, 59 mg (1.20 mmol) of sodium cyanide, 4-bromo-N,
200 mg (1.00 mmol) of N-dimethylaniline
And the atmosphere in the reaction vessel was replaced with argon. Then, at room temperature, 1.7 mL of a mixed solvent of methanol and acetic acid (volume ratio: 3/1) was used.
Was added. 280 mg of 30% hydrogen peroxide solution
Was added dropwise over 1 hour. After completion of the dropwise addition, the mixture was stirred at room temperature for 2 hours, 5 ml of a 5% aqueous sodium sulfite solution was added to decompose the remaining hydrogen peroxide, and saturated aqueous sodium hydrogen carbonate was added to make the reaction mixture alkaline. 1 with 10 mL of ethyl acetate
The extract was washed twice with saturated sodium chloride solution and dried over sodium sulfate to obtain a solution of 4-bromo-N-cyanomethyl-N-methylaniline in ethyl acetate. . When the solution was analyzed by gas chromatography internal standard method, the conversion of 4-bromo-N, N-dimethylaniline was 97%, and the yield of 4-bromo-N-cyanomethyl-N-methylaniline was 67% ( Vs. 4
-Bromo-N, N-dimethylaniline). The yield of N- (4-bromophenyl) -N-methylformamide, a by-product, was 5% (vs. 4-bromo-N, N-dimethylaniline).

Example 5 Ruthenium chloride hydrate (13 mg, 0.05 mmol) and sodium cyanide (59 mg, 1.20 mmol) were placed in a 25 mL-equipped branched eggplant flask, and the inside of the reaction vessel was purged with argon. Then, at room temperature, 1.7 mL of a mixed solvent of methanol and acetic acid (3/1 by volume), N-ethyl-N-
135 mg (1.00 mmol) of methylaniline were added. To this mixture, 280 mg of 30% aqueous hydrogen peroxide was added dropwise over 1 hour. After completion of the dropwise addition, the mixture was stirred at room temperature for 1 hour, 5 ml of a 5% aqueous sodium sulfite solution was added to decompose the remaining hydrogen peroxide, and saturated aqueous sodium hydrogen carbonate was added to make the reaction mixture alkaline. 5m once with 10mL of ethyl acetate
L, extract twice, wash the resulting extract with saturated saline, dry over sodium sulfate, and add 4-bromo-N
-A solution of -cyanomethyl-N-methylaniline in ethyl acetate was obtained. When the solution was analyzed by gas chromatography internal standard method, the conversion of 4-bromo-N, N-dimethylaniline was 98% and the yield of N-cyanomethyl-N-ethylaniline was 58% (vs. 4-bromo-N-ethylaniline). -N, N-dimethylaniline).

Example 6 13 mg (0.05 mmol) of ruthenium chloride hydrate and 59 mg (1.20 mmol) of sodium cyanide were put into a 25 mL-equipped eggplant flask with an inner volume, and the inside of the reaction vessel was purged with argon. Then, at room temperature, 1.7 mL of a methanol-acetic acid mixed solvent (3/1 by volume) and 161 mg (1.00 mmol) of N-phenylpiperidine were added. To this mixture, 280 mg of 30% aqueous hydrogen peroxide was added dropwise over 1 hour. After completion of dropping, the mixture was stirred at room temperature for 1 hour, and then 5%
The remaining hydrogen peroxide was decomposed by adding 5 ml of an aqueous solution of sodium sulfite, and saturated aqueous sodium hydrogen carbonate was added to make the reaction mixture alkaline. Once in 10 mL of ethyl acetate, 2 in 5 mL
The extract was washed once, and the obtained extract was washed with saturated saline, dried over sodium sulfate, and concentrated to obtain crude 2-cyano-N-phenylpiperidine. Crude 2-cyano-N-
When phenylpiperidine was analyzed by gas chromatography internal standard method, the conversion of N-phenylpiperidine was 87%. When the crude 2-cyano-N-phenylpiperidine was analyzed by NMR, the yield of 2-cyano-N-phenylpiperidine was 69% (vs.
Phenylpiperidine). The crude 2-cyano-N-phenylpiperidine was subjected to silica gel chromatography to give 2-cyano-N-phenylpiperidine in an isolated yield of 61%.

Example 7 Ruthenium chloride hydrate (13 mg, 0.05 mmol) and sodium cyanide (59 mg, 1.20 mmol) were placed in a 25 mL-equipped eggplant-shaped flask with a branch volume, and the inside of the reaction vessel was purged with argon. Then, at room temperature, 1.7 mL of a mixed solvent of methanol and acetic acid (3/1 by volume) and 191 mg of N- (4-methoxyphenyl) piperidine (1.00 mmol) were used.
l) was added. This mixture is mixed with 30% aqueous hydrogen peroxide 170
mg was added dropwise over 1 hour. After completion of the dropwise addition, the mixture was stirred at room temperature for 1 hour, 5 ml of a 5% aqueous sodium sulfite solution was added to decompose the remaining hydrogen peroxide, and saturated aqueous sodium hydrogen carbonate was added to make the reaction mixture alkaline. Extraction was performed once with 10 mL of ethyl acetate and twice with 5 mL, and the obtained extract was washed with saturated saline, dried over sodium sulfate, and concentrated to give crude 2-cyano-N- (4- Methoxyphenyl) piperidine was obtained. The crude 2-cyano-N- (4-methoxyphenyl) piperidine was analyzed by gas chromatography internal standard method to find N- (4-methoxyphenyl) piperidine.
The piperidine conversion was 92%. Further, crude 2-cyano-N- (4-methoxyphenyl) piperidine was converted to NM.
When analyzed by R, the yield of 2-cyano-N- (4-methoxyphenyl) piperidine was 73% (vs. N- (4
-Methoxyphenyl) piperidine). The crude 2-cyano-N- (4-methoxyphenyl) piperidine is subjected to silica gel chromatography to give 2-cyano-N-
(4-methoxyphenyl) piperidine was isolated at a yield of 58%.
I got it. Colorless solid IR (KBr) 2959, 2926, 2226, 1586, 1512, 145
6, 1291, 1244, 1211,1183, 1036, 934, 860, 8
29, 798, 716, 534 cm ^-1 1H NMR (CDCl ₃ , 270 MHz) d 1.62-1.88 (m, 4
H), 2.02 (m, 2 H), 3.02 (td, J = 11.5 and
2.4 Hz, 1 H, 6-H ax), 3.23 (dm, J = 12.0
Hz, 1 H, 6-H eq), 3.77 (s, 3 H, CH ₃ O),
4.44 (t, J = 3.4 Hz, 1 H, NCHCN), 6.85 (d
m, J = 9.3Hz, 2H, ArH), 6.98 (dm, J =
9.0 Hz, 2 H, ArH) 13C NMR (CDCl ₃ , 68 MHz) d 155.5, 143.8, 12
0.7, 117.2, 114.6, 55.5, 53.8, 47.3, 29.4, 2
5.2, 20.1 Anal.Calcd for C13H16N2O: C, 72.19; H, 7.4
6; N, 12.95; O, 7.40. Found C, 72.25; H,
7.62; N, 13.02; O, 7.11

COMPARATIVE EXAMPLE 13 mg (0.05 mmol) of ruthenium chloride hydrate was placed in a 25 mL-equipped eggplant-shaped flask with a branch volume, and the inside of the reaction vessel was purged with argon. Then 1.7m ethyl acetate at room temperature
121 mg of L, N, N-dimethylaniline (1.00 m
mol) was added. To this mixture were added 760 mg (3.00 mmol) of a 30% ethyl peracetic acid solution and 198 mg (2.00 mmol) of trimethylsilyl cyanide.
It was dropped over time. After completion of the dropwise addition, the mixture was stirred at room temperature for 23 hours, and 5 mL of a 5% aqueous solution of sodium sulfite was added to decompose peracetic acid. Perform extraction treatment twice with 5 mL of ethyl acetate,
The obtained extract was washed with saturated saline, dried over sodium sulfate, and concentrated to obtain crude N-phenyl-N-methylaminoacetonitrile. Crude N-phenyl-N-methylaminoacetonitrile is subjected to silica gel column chromatography to isolate N-phenyl-N-methylaminoacetonitrile in an isolated yield of 75% (vs. N, N-dimethylaniline), a by-product. N-methyl-N-phenylformamide was obtained in an isolated yield of 14% (vs. N, N-dimethylaniline).

Reference Example Synthesis of α-amino acid from α-aminonitrile 46.3 mg of N- (4-methoxyphenyl) -N-methylaminoacetonitrile obtained according to Example 1.
(0.263 mmol) was placed in a 25 mL branched flask with an internal volume of 25 mL, and the reaction vessel was purged with argon gas. 20.5 mL of an ethanol solution of 50.5 mg (1.26 mmol) of sodium hydroxide was added, and the mixture was refluxed at an internal temperature of 90 ° C. for 5 hours. The reaction mixture was cooled to room temperature, and the deposited precipitate was collected by filtration, washed three times with 1 mL of ice-cooled ethanol, dried under reduced pressure, and dried to obtain 42.3 mg of N- (4-methoxyphenyl) -N-methylglycine (0. .217 mmol) (yield 8).
3% vs. N- (4-methoxyphenyl) -N-methylaminoacetonitrile). Colorless solid; mp 157-159 ° C IR (KBr) 3304, 3167, 1633, 1601, 1397, 132
7, 1257, 1242, 1211,1184, 1039, 945, 806, 7
21 cm ^-1 1H NMR (CDCl ₃ , 270 MHz) 2.96 (s, 3 H, NC
H ₃ ), 3.76 (s, 5 H, overlapped, CH ₃ O and NC
H ₂ ), 6.59 (br, 1 H, COOH), 6.74 (dm, J =
9.0 Hz, 2H, ArH), 6.86 (dm, J = 9.0 Hz,
2 H, ArH) 13C NMR ( CDCl 3, 68 MHz) 173.7, 153.2, 143.
2, 115.2, 114.9, 59.4, 55.7, 40.6

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁶ Identification symbol FI C07C 255/43 C07C 255/43 // C07B 61/00 300 C07B 61/00 300

Claims (4)

[Claims] 1. The general formula (1) (Wherein, R ¹ represents an optionally substituted phenyl group, R ² represents an alkyl group or an optionally substituted phenyl group, and R ³ represents a hydrogen atom, an alkyl group or an optionally substituted And R ² and R ³ may combine to form a nitrogen-containing ring) with a cyanide in the presence of a transition metal catalyst and hydrogen peroxide. General formula (2) characterized by reacting (Wherein R ¹ , R ² and R ³ have the same meanings as described above). 2. The method for producing α-aminonitrile according to claim 1, wherein the cyanide is an alkali metal cyanide or hydrogen cyanide. 3. The α according to claim 2, wherein the alkali metal cyanide is sodium cyanide or potassium cyanide.
-A process for producing aminonitrile. 4. The method for producing α-aminonitrile according to claim 1, wherein the transition metal catalyst is ruthenium halide, iron halide, or manganese halide.