JPH0217164A - Production of alpha-aminophenylacetonitrile hydrochloride - Google Patents

Abstract

PURPOSE:To advantageously obtain the title compound used for a raw material agricultural chemical and medicine without lowering decomposition yield by reacting reaction product of benzaldehydes with hydrogen cyanide with ammonia in acetonitrile and then directly depositing the title compound as hydrochloride thereof by hydrochloric acid. CONSTITUTION:Benzaldehydes expressed by formula I (X is halogen, 1-6C lower alkyl, 1-6C lower alkoxy, trifluoromethyl, methylenedioxy or hydroxyl group; n is 0-2) are reacted with hydrogen cyanide in a solvent such as methanol using triethylamine as a catalyst to afford alpha-cyanobenzyl alcohols expressed by formula II, which are then reacted with ammonia in acetonitrile at 20-80 deg.C, preferably 40-60 deg.C for 0.5-8hr to give a compound expressed by formula III. After finishing the reaction, excess ammonia is removed by reduced pressure, etc., and them concentrated hydrochloric acid is dropwise added to the compound expressed by formula III at ambient temperature in equimolar amount based on the compound expressed by formula III without requiring other after-treatment such as removal of solvent to provide the compound expressed by formula IV.

Description

[Detailed description of the invention]

[Industrial Field of Application] The present invention relates to a method for producing α-aminophenylacetonitrile hydrochloride, which is useful as a raw material for agricultural chemicals and medicines. [Prior art and problems to be solved by the invention] α-aminophenylacetonitrile hydrochlorides (hereinafter referred to as α- As for the manufacturing method of aminophenylacetonitrile hydrochloride), please refer to ■Journal of American Chemical Society (J^C5)] Niji 5991 (195
8), ■Journal of Medicinal Chemistry*
is try) and 901 (1973). In method (2), potassium chloride and ammonium chloride are reacted with benzaldehyde in a water-methanol mixed solvent system to form α-aminophenyl acetonitrile, then the solvent is replaced with ether, hydrogen cyanide gas is introduced, and α-
Aminophenylacetonitrile hydrochloride is produced in 13% yield. In method (2), a sulfite adduct of benzaldehyde is generated in advance in water, and aqueous ammonia and then sodium cyanide are added to react. It is known that α-7 minophenyl acetonitrile is extracted from water and added to a hydrogen chloride and ethanol solution to produce α-aminophenyl acetonitrile hydrochloride in a yield of 509 g. In any of the above synthetic methods using the Strenker reaction, the desired product was not obtained in a satisfactory yield, and in all cases, α-aminophenylacetonitrile hydrochloride was obtained using hydrogen chloride gas. This makes the operation complicated and highly dangerous, and requires solvent removal, solvent replacement, dehydration, or extraction operations. Therefore, it is necessary to handle α-aminophenyl acetonitrile in a free state, which causes problems of deterioration of yield and purity due to decomposition and coloration. The present invention provides α-aminophenyl acetonitrile (hereinafter referred to as α-aminophenyl acetonitrile) represented by the formula (wherein, X is the same as the single-layer formula (1)) without using any special reagent. In order to avoid a decrease in yield due to decomposition and coloration, the reaction is carried out in acetonitrile, eliminating the need for operations such as removing and replacing the solvent. The object of the present invention is to provide a method for producing α-aminophenylacetonitrile hydrochlorides. [Means and operations for solving the L\problem] In order to achieve the above object, the present inventors have conducted various studies on methods for solving such a problem, and as a result, -formation (1) (in the formula , X represents a halogen atom, a C1 to C6 lower alkyl group, a C4 to C6 lower alkoxy group, a trifluoromethyl group, a methylenedioxy group, or a hydroxyl group, and n is 0 to 2.
Benzaldehydes (hereinafter referred to as benzaldehydes) represented by α-cyanobenzyl alcohols (hereinafter referred to as α-cyanobenzyl alcohols) are reacted with ammonia in acetonitrile, and the resulting α-aminophenyl acetonitrile is precipitated as a hydrochloride with hydrochloric acid in acetonitrile. The present inventors have discovered that α-aminophenylacetonitrile hydrochlorides can be obtained with high purity and high yield without performing operations such as removing the solvent or converting the solvent to y1, and have completed the present invention. That is, in the present invention, benzaldehydes are reacted with hydrogen cyanide, the obtained α-cyanobenzyl alcohols are reacted with ammonia in acetonitrile, and the obtained α-aminophenyl acetonitrile is reacted with hydrochloric acid in acetonitrile. This is a method for producing α-aminophenylacetonitrile hydrochloride, which is characterized by precipitating it as a salt. Next, the present invention will be explained in detail. Examples of the benzaldehydes used in the present invention include:
Benzaldehyde, O-fluorobenzaldehyde, O
-chlorobenzaldehyde, 0-bromobenzaldehyde, O-iodobenzaldehyde, 0-tolualdehyde, 0-ethylbenzaldehyde, 0-(n-propyl)
Benzaldehyde, 0-(iso-propyl)benzaldehyde, 0-(n-butyl)benzaldehyde, 0-
(iso-butyl)benzaldehyde, 0- (see
-butylbenzaldehyde, 0-(tert-butyl)benzaldehyde, 0-(n-pentyl)benzaldehyde, 0-(l-methylbutyl)benzaldehyde,
0-(2-methylbutyl)benzaldehyde, 0-(3
-Methylbutyl)benzaldehyde, 0-(1,1-dimethylpropyl)benzaldehyde, 0-(1,2-dimethylpropyl)benzaldehyde, 0-<2.2-
dimethylpropyl)benzaldehyde, 0-(l-ethylpropyl)benzaldehyde, Q-(nhexyl)benzaldehyde, 0-(1-methylpentyl)benzaldehyde, 0-(2-methylpentyl)benzaldehyde, 0-(3-methyl) pentyl) benzaldehyde, 0
-(4-methylpentyl)benzaldehyde, 0-(1
, 1-dimethylbutyl)benzaldehyde, 0-(1,
2-dimethylbutyl)benzaldehyde, 0-(1,3
-dimethylbutyl)benzaldehyde, 0-(2,2-
dimethylbutyl)benzaldehyde, 0-(2,3-dimethylbutyl)benzaldehyde, 0-(3,3-dimethylbutyl)benzaldehyde, -fluorobenzaldehyde, -chlorobenzaldehyde, tofuromobenzaldehyde, di-iodobenzaldehyde, di-tolualdehyde , toethylhensaldehyde, m-(n-propyl)benzaldehyde, intestinal-(iso-propyl)benzaldehyde, intestinal-(n-)゛chilshi) penzua! Redehyde, m-(iso-)ethyl)benzaldehyde, -
(see-butyl)benzaldehyde, zen-(LerL
-)゛thyl)benzaldehyde, LR-(n-pentyl)benzaldehyde, ■-(1-methylbutyl)benzaldehyde, tho(2-methylbutyl)benzaldehyde, 5-(3-methylbutyl)penzaldehyde, 5-(
1,1-dimethypropylun aldehyde, -(1.
2-dimethylpropylon aldehyde, @-(2.2-
dimethylpropyl)benzaldehyde, s-(1-ethylJ leprovir)benzaldehyde, m-(n-hexyl)benzaldehyde, s-(1-methylpentyl)benzaldehyde, t(2-methylpentyltylpentylpentyl)benzaldehyde, s-( 1.1-dimethylbutyl)benzaldehyde, m-(1.2-dimethylbutyl)benzaldehyde, s-(1.3-dimethyl)ethyl)benzaldehyde, s-(2.2-dimethylbutyl)benzaldehyde, ■-( 2.3-dimethylbutyl)penzaldehyde, -1(3.3-dimethylbutyl)benzaldehyde, P-fluorobenzaldehyde,
P-chlorobenzaldehyde, P-bromobenzaldehyde, P-iodobenzaldehyde, P-)raldehyde, P-ethylbenzaldehyde, P-(n-propyl)benzaldehyde, P-(iso-brovirpenzalte'human, P-( n-]゛Titylunsaldehyde, P-(iso-butyl)benzaldehyde, P- (
sec-butyl)benzaldehyde, P-(ter

[−
butyl)benzaldehyde, P-(n-pentyl)benzaldehyde, P-(1-methylbutyl)benzaldehyde, P-(2-methylbutyl)benzaldehyde,
P-(3-methylbutyl)benzaldehyde, P-(1
．． 1-dimethylpropyl)benzaldehyde, P-(1
．． 2-dimethylpropyl)benzaldehyde, P-(2
2-dimethylpropyl)benzaldehyde, P-(1
Ethylpropyl)benzaldehyde, P-(n-hexyl)benzaldehyde, P-(1-methylpentyl)benzaldehyde, P-(2-methylpentyl)benzaldehyde, P-(3-methylpentyl)benzaldehyde, P-(4-methyl pentyl)benzaldehyde, P
-(1,1-dimethylbutyl)benzaldehyde, P-
(1.2~dimethylbutyl)benzaldehyde, P-(
1.3-dimethylbutyl)penzaldehyde, P-(2
,2-dimethylbutyl)benzaldehyde, P-(2,
3-dimethylbutyl)benzaldehyde, P-(3,3
, dimethylbutyl)benzaldehyde, 0-(1ethylbutyl)benzaldehyde, 0-(2-ethylbutyl)
Benzaldehyde, 0-methoxybenzaldehyde, 0
-ethoxybenzaldehyde, 0-(n, propoxy)
Benzaldehyde, 0-(iso-propoxy)benzaldehyde, 0-(n,butoxy)benzaldehyde,
0-(n-butoxy)benzaldehyde, 0-(iso
-butoxy)benzaldehyde 1, 〇-(see-butoxy)benzaldehyde, 0-(tert-butoxy)
Benzaldehyde, 0-trifluoromethylbenzaldehyde, 2,3-methylenedioxybenzaldehyde,
0-Hydroxybenzaldehyde, 2.3-difluorobenzaldehydrobenzaldehyde, 2.3-dichlorobenzaldehyde, 2.6-dichlorobenzaldehyde, 2,3-dimethylbenzaldehyde, 2.6-diethylbenzaldehyde, 2.3-diethylbenzaldehyde, 2 .6-diethylbenzaldehyde, 2.3-dimethoxybenzaldehyde, 2.6-dimethoxybenzaldehyde, 2,
3-dihydroxybenzaldehyde, 2,6-dihydroxybenzaldehyde, 2,3-ditrifluoromethylbenzaldehyde, 2,6 ditrifluoromethylhenzaldehyde, ++-(1-ethylbutyl)benzaldehyde, tho(2-ethylbutyl)benzaldehyde, -methoxybenzaldehyde , -ethoxybenzaldehyde, s-(n-propoxy)benzaldehyde, m-C
:so-propoxy)benzaldehyde, s-(n-
butoxy)benzaldehyde, -(iSO-butoxy)
Benzaldehyde, m-(sec-butoxy)benzaldehyde, terL-butoxy)benzaldehyde, -trifluoromethylbenzaldehyde, 3.4
-Methylenedioxybenzaldehyde, hydroxybenzaldehyde, 2,4-difluorobenzaldehyde, 3,4-difluorobenzaldehyde, 2,4-dichlorobenzaldehyde, 3,4-dichlorobenzaldehyde, 2,4-dimethylbenzaldehyde, 3,4-dimethyl Benzaldehyde, 2. 4-diethylbenzaldehyde, 3,4-diethylbenzaldehyde, 2,4,dimethoxybenzaldehyde,
34-dimethoxybenzaldehyde, 2.4-dihydroxybenzaldehyde, 3.4-dihydroxybenzaldehyde, 2.4-ditrifluoromethylbenzaldehyde, 3.4-ditrifluoromethylbenzaldehyde, P- (1-ethylbutyl)benzaldehyde, P-
(2-Ethylbutyl)benzaldehyde, P-methoxybenzaldehyde, P-ethoxybenzaldehyde, P
-(n-propoxy)benzaldehyde, P-(iso
-propoxy)benzaldehyde, 'P-(n-butoxy)benzaldehyde, P-(iso-butoxy)
Benzaldehyde, P-(see-butoxy)benzaldehyde, P-(terdibutoxy)benzaldehyde, P-trifluoromethylbenzaldehyde, P-hydroxybenzaldehyde, 2.5-difluorobenzaldehyde, 3.5-difluorobenzaldehyde, 2,
5-dichlorobenzaldehyde, 3.5-dichlorobenzaldehyde, 2.5-dimethylbenzaldehyde, 3
, 5-dimethylbenzaldehyde, 2.5-diethylbenzaldehyde, 3I5. diethylbenzaldehyde,
2,5-dimethoxybenzaldehyde, 3,5-dimethoxybenzaldehyde, 2,5-dihydroxybenzaldehyde, 3,5-dihydroxybenzaldehyde, 2
, 5-ditrifluoromethylbenzaldehyde, 35-
Examples include ditrifluoromethylbenzaldehyde, but are not necessarily limited thereto. α-Cyanobenzyl alcohols are synthesized from benzaldehydes and hydrogen cyanide according to known methods. No solvent or 30% solvent per mole of penzaltehyde
Add 0ml or less. The solvent is not particularly limited as long as it is inert to the reaction, but alcohols such as methanol and ethanol, ethers such as diethyl ether and tetrahydrofuran, and acetonitrile are preferred. If the amount of solvent is large, it does not affect the yield, but it is not preferred industrially. In this solution, triethylamine, pyridine,
Organic bases such as N,N-dimethylethanolamine, organic acid salts such as sodium acetate and sodium oxalate, weak alkaline bases such as alkali cyanides such as sodium cyanide and potassium cyanide, etc. 20 to 1000 PPs, preferably 100 to 5 OOPPs Add as follows. Hydrogen cyanide is added dropwise to this solution at a temperature range of 0 to 20°C. The amount of hydrogen cyanide dropped is Benzaldehyde I
The amount is 1 to 10 mol per 11 mol, and if the amount is large, it will not affect the yield at all, but it is not preferred industrially.
Continue stirring for ~10 hours. After the reaction is complete, excess hydrogen cyanide and solvent are removed under reduced pressure or by introducing nitrogen gas. Acetonitrile is 0.1 to 21, preferably 0.125 to 1 mol of α, cyanobenzyl alcohol fi produced.
~1.21 is added and dissolved, and ammonia is introduced while stirring and heating. The amount of ammonia used is 1 to 20 mol, preferably 1 to 10 mol, per 1 mol of α-cyanobenzyl alcohol. The flow rate of ammonia introduced is 10 to 1011 hours. The temperature at which ammonia is introduced is 20 to 80°C, preferably 40 to 60°C. The reaction time should be between 0.5 and sR, but usually between 3 and 5 sR.
Often completed in time. After the reaction is completed, excess ammonia is removed under reduced pressure or by introducing nitrogen gas. Other methods include solvent removal, solvent replacement, and dehydration.
No post-processing required. Next, a predetermined amount of concentrated hydrochloric acid is added dropwise at room temperature to precipitate α-aminophenylacetonitrile as a hydrochloride, and α-aminoacetonitrile hydrochloride is filtered out as crystals to obtain highly purified α-aminoacetonitrile hydrochloride. can be obtained. The amount of concentrated hydrochloric acid to be used can actually be used in the range of 0.8 to 1.2 mol per 111 mol of α-aminophenylacetonitrile, but the closer it is to equimolar, the higher the yield; is preferable, if it is small, α as hydrochloride
- Aminophenylacetonitrile cannot be recovered completely,
If it is in excess, α-aminophenylacetonitrile hydrochloride will dissolve and the recovery rate as crystals will decrease. [Example] Below, real J! The present invention will be specifically explained by way of examples. Yields in the examples were determined by titration. Example 1 Add 0.2 g of sodium acetate to 212 g (2 mol) of benzaldehyde, and while keeping the temperature around 10°C in a cold water bath, add 90% of hydrogen cyanide while stirring so that the internal temperature does not exceed 15°C.
1 liter was added dropwise over 1.5 hours. Another 3 hours, 10
Stirring was continued at around ℃. After the reaction was completed, excess hydrogen cyanide was removed by introducing nitrogen gas at room temperature to obtain crude α-cyanobenzyl alcohol. This was dissolved in 21 hours of acetonitrile, heated to 55° C., and ammonia gas was introduced at a flow rate of 301 hours while stirring. After 1 hour, the reaction was completed. After the reaction solution was returned to room temperature and excess ammonia was removed under reduced pressure, 62 liters of reduced salt #I was clarified, precipitated crystals were separated by filtration, and dried. As a result, 248 g of α-aminophenylacetonitrile was obtained. The purity was 98.2% and the yield was 74.1%. Example 2 24 g of 4-hydroquine benzaldehyde F (0,2'E
), sodium acetate A 0.02g, methanol 511
Add hydrogen cyanide 15 and keep it at around 15 °C in a cold water bath, and add hydrogen cyanide 15 while stirring so that the internal temperature does not exceed 18 °C.
ml was added dropwise over 1.0 hour. Another 3 hours, 1
Stirring was continued at around 5°C. After the reaction was completed, methanol and excess hydrogen cyanide were removed under reduced pressure, and crude α-cyano P-hydroxybenzyl alcohol was dissolved in heptonitrile, heated to 50°C, and heated to 51° C. with stirring.
Ammonia gas was introduced at a flow rate of /h. After 3.0 hours, the reaction was completed. After returning the reaction solution to room temperature and removing excess ammonia under reduced pressure, concentrated hydrochloric acid 13*j! was added dropwise, and the precipitated crystals were filtered and dried. As a result, 25.9 g of α-amino-P-hydroxyphenylacetonitrile hydrochloride was obtained. Purity 97
．． The yield was 71.3%. Example 3 16.6 g of 34-dimethoxybenzaldehyde (0,
1 mole), sodium acetate 0.005 g, methanol 5
-j! While maintaining IQ'C around IQ'C in a cold water bath,
Under RET, 8 ml of hydrogen cyanide was added dropwise over 1.0 hour. Stirring was continued at around 12°C for an additional 2 hours. After the reaction was completed, excess hydrogen cyanide and methanol were removed under reduced pressure to obtain crude α-cyano-364-dimethoxyhensyl alcohol. This was dissolved in 100 se of acetonitrile, heated to 50° C., and ammonia gas was introduced at a flow rate of 317 hours while stirring. After 3.5 hours, the reaction was completed. After returning the reaction solution to room temperature and removing excess ammonia by introducing nitrogen gas, 6.1 ml of 12N hydrochloric acid was added dropwise, and the precipitated crystals were filtered and dried. As a result, α-amino-3,
16.4-dimethoxyphenylacetonitrile hydrochloride.
I got 1g. The purity was 99.2% and the yield was 70.5%. Example 4 4-chlorobenzaldehyde 14.0 g (0.1 mol)
0.005 g of sodium acetate and methanol 5-1 were added thereto, and hydrogen cyanide 8-2 was added dropwise over 1.0 hour while stirring while maintaining the temperature at around 10°C in a cold water bath. 3 more
Stirring was continued at around 5°C for an hour. After the reaction was completed, excess hydrogen cyanide and methanol were removed under reduced pressure to obtain crude α-cyano-4-chlorohensyl alcohol. This was dissolved in 100 l of acetonitrile, heated to 45°C, and ammonia gas was introduced at a flow rate of 327 hours while stirring. After 3.0 hours, the reaction was completed. After the reaction solution was returned to room temperature and excess ammonia was removed under reduced pressure, 6,3 tal of concentrated hydrochloric acid was added dropwise, and the precipitated crystals were filtered and dried. As a result, 13.8 g of α-amino, 4-chlorophenylacetonitrile hydrochloride was obtained. Purity 98
．． The yield was 67.8%. Example 5 17.4 g of 0-trifluoromethylbenzaldehyde (
0.1 mol), add 0.005 g of sodium acetate and 5-l of methanol, and while keeping it around IO'C in a cold water bath,
While stirring, 81 Il of hydrogen cyanide was added dropwise over 1.0 hour. Stirring was continued at around 15°C for an additional 3 hours. After the reaction was completed, excess hydrogen cyanide and methanol were removed under reduced pressure to obtain crude α-cyano-2-trifluoromethylbenzyl alcohol. Dissolve this in looml acetonitrile), warm to 45°C, and stir. l lower, 31/
Ammonia gas was introduced at a flow rate between let. After 3.5 hours, the reaction was completed. After returning the reaction solution to room temperature and removing excess ammonia under reduced pressure, 6.5sj! of concentrated hydrochloric acid was added. was added dropwise, and the precipitated crystals were filtered and dried. As a result, 17.5g of α-amino-2-trifluoromethylphenylacetonitrile hydrochloride
18, purity 97.8%, yield 74.0%. Example 6 Tomethoxybenzaldehyde 13.6g (0.1 mol)
0.005 g of sodium acetate and 5 sf of methanol were added to the mixture, and while the temperature was maintained at around 10°C in a cold water bath, 8.2 cm of hydrogen cyanide was added dropwise over 1.0 hour while stirring. 3 more
Time, around 15°C! II l'l! continued. After the reaction was completed, excess hydrogen cyanide and methanol were removed under reduced pressure, dissolved in crude Noano 3-methoxybenzyl alcohol nitrile, heated to 45°C, and mixed with 3 Jl under stirring.
! Ammonia gas was introduced at a flow rate of /hour. After 3.0 hours, the reaction was completed. After the reaction solution was returned to room temperature and excess ammonia was removed under reduced pressure, 6.4 cm2 of concentrated hydrochloric acid was added dropwise, and the precipitated crystals were filtered and dried. As a result, 14.9 g of α-amino-3-methoxyphenylacetonitrile hydrochloride was obtained. Purity 98
．． The yield was 75.0%. Example 7 15.0 g of 3,4-methylenedioxybenzaldehyde
(0.1 mol) was added with 0,005 g of sodium acetate and 5 ml of methanol, and kept at around 10°C in a cold water bath.
While stirring, hydrogen cyanide 8-2 was added dropwise over 1.0 hour. llt4' was continued for an additional 3 hours at around 15°C. After the reaction was completed, excess hydrogen cyanide and methanol were removed under reduced pressure to obtain crude α-cyano-3,4-methylenedioxybenzyl alcohol. This was dissolved in 100 wl of acetonitrile, heated to 45°C, and ammonia gas was introduced at a flow rate of 31/hour while stirring. 3.0 hours later,
The reaction has ended. After the reaction solution was returned to room temperature and excess ammonia was removed under reduced pressure, 6.5 ml of tetrahydrochloric acid was added dropwise, and the precipitated crystals were filtered and dried. As a result, 14.8 g of α-amino-3°4-methylenedioxyphenylacetonitrile hydrochloride was obtained. The purity was 98.0% and the yield was 69.6%. Example 8 4-ethylbenzaldehyde 13.4g (0.1 mol)
Add 0.005 g of sodium acetate and 5 i of methanol to the mixture, and while stirring while keeping the temperature around 10°C in a cold water bath, add 8 coats of hydrogen cyanide! was added dropwise over 1.0 hour. 3 more
Stirring was continued at around 15°C for an hour. After the reaction was completed, excess hydrogen cyanide and methanol were removed under reduced pressure to obtain crude α-cyano 4-ethylbenzyl alcohol. This was dissolved in 100 liters of acetonitrile, heated to 45°C, and ammonia gas was introduced at a flow rate of 3 L' while stirring. After 3.0 hours, the reaction was completed. After the reaction solution was returned to room temperature and excess ammonia was removed under reduced pressure, 6.3 ml of concentrated hydrochloric acid was added dropwise, and the precipitated crystals were filtered and dried. As a result, 1 ton (13.8 g) of α-amino-4-ethylphenylacetonitrile hydrochloride was obtained. Purity 98
．． The yield was 70.2%. Comparative Example 1 21.2 g (0.2 mol) of benzaldehyde in methanol j9M50mz was added dropwise to 50 ml of an aqueous solution of 12 g of ammonium chloride and 10 g of sodium cyanide. After completion of the 8 dropwise additions, the mixture was stirred for 7 hours. After the reaction was completed, 200 ml of water was added, methanol was removed under reduced pressure, and the mixture was extracted three times with ether 2oollN. An ether solution saturated with hydrogen chloride gas was added dropwise to the crude α-aminophenylacetonitrile solution, and the precipitated crystals were filtered and dried. As a result, 11.6 g of α-aminophenylacetonitrile hydrochloride was obtained. Purity 87.2%,
The yield was 34.4%. (Effects of the Invention) Since the present invention does not use any special reaction reagent and the reaction is carried out in acetonitrile, there is no low yield due to decomposition or coloring of unstable α-aminophenyl acetonitrile, and This is an industrially useful method that can be used immediately in the next step without removing or replacing the solvent. Patent applicant Mitsui Toatsu Chemical Co., Ltd.

Claims (1)

[Claims] 1. General formula (I) ▲ Numerical formulas, chemical formulas, tables, etc. ▼ (I) (In the formula, X is a halogen atom, a lower alkyl group of C_1 to C_6, a lower alkoxy group of C_1 to C_6 , trifluoromethyl group, methylenedioxy group, hydroxyl group, n
represents an integer from 0 to 2. ) General formula (II) obtained by reacting benzaldehydes expressed by hydrogen cyanide with hydrogen cyanide ▲There are mathematical formulas, chemical formulas, tables, etc.▼(II) (In the formula, X is the same as general formula (I).) α−
The general formula (III) obtained by reacting cyanobenzyl alcohols with ammonia in acetonitrile ▲There are mathematical formulas, chemical formulas, tables, etc.▼(III) (In the formula, X is the same as the general formula (I).) α−
General formula (IV), which is characterized by precipitating aminophenylacetonitriles as a hydrochloride salt with hydrochloric acid in acetonitrile ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (IV) (In the formula, X is the general formula (I) and ) is expressed as α−
A method for producing aminophenylacetonitrile hydrochloride.