CN104418762B - A kind of method from aldehyde synthesizing amide - Google Patents
A kind of method from aldehyde synthesizing amide Download PDFInfo
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Abstract
The invention discloses a kind of method from aldehyde synthesizing amide.In reaction vessel, add aldehyde, oxammonium hydrochloride., alkali and water, react half an hour under room temperature；Aldehyde is completely converted into oxime, then, adds water solublity iridium complex, and reactant mixture is 80 120oUnder C after stoichiometric number hour, it is cooled to room temperature, selects evaporation to remove water, post isolated target product.Compared with one kettle way aldehyde and azanol reaction in water generate oxime, the method being rearranged to amide the most again is compared, and catalyst used in the present invention load is low, does not contains the Phosphine ligands that environmental pollution is serious, the most just can carry out, it is not necessary to nitrogen protection.Therefore, this reaction meets the requirement of Green Chemistry, has vast potential for future development.
Description
Technical field
The invention belongs to technical field of organic synthetic chemistry, be specifically related to a kind of method from aldehyde synthesizing amide.
Background technology
Amide is the critical function group of protein, be also normally used as intermediate synthesis fine chemicals, natural product and
Polymer etc..Traditional synthesizing amide method is to occur anti-by carboxylic acid derivates (such as, acyl chlorides, anhydride and ester) and ammonia
Should, although using widely, but the material toxicity that this method is used is relatively big, and has certain corrosivity to equipment,
Reaction discharges big energy, produces a large amount of spent acid, and simultaneously poor to the adaptability of some functional group, Atom economy is low.Separately
One is under conditions of strong acid and high temperature, by oxime through isomerization, occurs Beckmann rearrangement to directly generate purpose and produces
Thing amide, although this method Atom economy is higher, but severe reaction conditions, be easily generated by-product simultaneously, it is difficult to controls.These
Program to use poisonous or expensive reagent, produces a large amount of harmful by-product, and the functional group of substrate the most often changes.
In 2005, American Chemical Society Green Chemistry institute announce the synthesis of the Atom economy of amine be synthetic organic chemical art
Important challenge.
Along with the deterioration of environment, in organic synthesis field, development cascade reaction has become growing important.Pass through
One kettle way, from the aldehyde of commercialization, by and oxammonium hydrochloride., alkali reacts synthesis oxime, is then passed through crossing metal catalytic and sends out
Raw rearrangement reaction, direct synthesizing amide has caused to be paid close attention to widely.In 2007, Mizuno and partner reported
One uses water as solvent, is directly synthesized the example of amide from aldehyde.The catalysis used is heterogeneous Rh (OH) x/Al2O3
(4mol%).The defect of reaction is to need to carry out at 160 DEG C, and reacts and also generate the by-products such as nitrile.(H.Fujiwara,
Y.Ogasawara, K.Yamaguchi, N.Mizuno, Angew.Chem.Int.Ed.2007,46,5202-5205.).Recently,
Crochet, Cadierno and partner illustrate and use the homogeneous ruthenium catalyst [RuCl containing poisonous Phosphine ligands2(η6-
C6Me6){P(NMe2)3] (5mol%), in relatively mild temperature, nitrogen state is got off to realize aldehyde and is directly synthesized amide.
(R.Garcia-Alvarez, A.E.Diaz-Alvarez, P.Crochet, V.Cadierno, RSCAdv., 2013,3,5889-
5894)。
From the viewpoint of sustainable chemistry, developing new homogeneous of a class, without phosphine, the catalyst of low-load, at water
In, under air condition, realize resetting aldehyde obviously have great importance to amide.
Summary of the invention
It is an object of the present invention to provide a kind of from the new method of aldehyde synthesizing amide (Formulas I)
It comprises reactant aldehyde (Formula II)
With oxammonium hydrochloride. (formula III)
Reaction is to occur in the presence that catalyst existence, water do solvent, alkali.Its reaction expression is
Wherein, R is selected from aryl or single or multiple substituted aryl, preferably chlorophenyl, dichloro-phenyl, bromo phenyl, trifluoro
Aminomethyl phenyl, phenyl, aminomethyl phenyl or methoxyphenyl；R or selected from fat-based, preferably benzyl or amyl group.N=0 or 1.
The present invention is realized by following technical method:
In reaction vessel, add aldehyde, oxammonium hydrochloride., alkali (playing neutralization) and water, react half an hour under room temperature；Aldehyde is complete
Entirely being transformed into oxime, then, add water solublity iridium complex, reactant mixture after stoichiometric number hour, is cooled at 80-120 DEG C
Room temperature, selects evaporation to remove water, post isolated target product.
Wherein, water solublity homogeneous transition metal catalyst is metal iridium complex (IV), [Cp*Ir (H2O)3][X]2, (its
Middle Cp*=pentamethylcyclopentadienyl, X=OTf, BF4、PF6Or SO4 2-), transition-metal catalyst consumption is relative
It is 0.5-3mol% in aldehyde mol ratio；Described aldehyde is 1:1 with the mol ratio of oxammonium hydrochloride.；Described alkali rubs with oxammonium hydrochloride.
That ratio is 1:2；Reaction temperature is 80～120 DEG C；Response time is 4～12 hours.
The invention have the advantage that
Compared with one kettle way aldehyde and azanol reaction in water generate oxime, the method being rearranged to amide the most again is compared, this
The catalyst load that invention is used is low, does not contains the Phosphine ligands that environmental pollution is serious, the most just can carry out, it is not necessary to nitrogen
Gas shielded.Therefore, this reaction meets the requirement of Green Chemistry, has vast potential for future development.
Detailed description of the invention
Show that example is to illustrate certain embodiments of the present invention, and should not be construed as restriction the scope of the present invention.Right
Present disclosure can carry out many improvement on material, method and reaction condition simultaneously, changes and changes.All this
A little improve, change and change and fall within the spirit and scope of the present invention the most definitely.
Embodiment 1:4-chlorobenzamide
4-chlorobenzamide
By 4-chlorobenzaldehyde (70.3mg, 0.5mmol), oxammonium hydrochloride. (34.7mg, 0.5mmol), sodium carbonate (26.5mg,
0.25mmol) it is sequentially added in 25ml Schlenk reaction bulb with water (1ml), after room temperature reaction half an hour, adds [Cp*Ir
(H2O)3][OTf]2(5.1mg, 0.0075mmol, 1.5mol%), after reactant mixture reacts 12 hours at 110 DEG C, cooling
To room temperature, rotary evaporation removes water, post isolated target compound, productivity: 85%.1H NMR (500MHz, DMSO-d6)δ
8.06 (br s, 1H, NH), 7.88 (d, J=8.4Hz, 2H, ArH), 7.52 (d, J=8.4Hz, 2H, ArH), 7.48 (br s, 1H,
NH)；13C NMR (125MHz, DMSO-d6) δ 166.8,136.1,133.0,129.4,128.3.
Embodiment 2:3,4-dichloro-benzamide
3.4-dichlorobenzamide
By 3,4-dichlorobenzaldehyde (87.5mg, 0.5mmol), oxammonium hydrochloride. (34.7mg, 0.5mmol), sodium carbonate
(26.5mg, 0.25mmol) and water (1ml) are sequentially added in 25ml Schlenk reaction bulb, after room temperature reaction half an hour, then add
Enter [Cp*Ir (H2O)3][OTf]2(5.1mg, 0.0075mmol, 1.5mol%), reactant mixture reacts 12 hours at 110 DEG C
After, it being cooled to room temperature, rotary evaporation removes water, post isolated target compound, productivity: 80%.
1H NMR (500MHz, DMSO-d6) δ 8.15 (br s, 1H, NH), 8.10 (s, 1H, ArH), 7.84 (d, J=8.2Hz,
1H, ArH), 7.75 (d, J=8.6Hz, 1H, ArH), 7.62 (br s, 1H, NH)；13C NMR (125MHz, DMSO-d6)δ
165.5,134.6,134.0,131.2,130.6,129.4,127.7.
Embodiment 3:4-brombenzamide
4-bromobenzamide
By 4-bromobenzaldehyde (92.5mg, 0.5mmol), oxammonium hydrochloride. (34.7mg, 0.5mmol), sodium carbonate (26.5mg,
0.25mmol) it is sequentially added in 25ml Schlenk reaction bulb with water (1ml), after room temperature reaction half an hour, adds [Cp*Ir
(H2O)3][OTf]2(10.2mg, 0.0150mmol, 3mol%), after reactant mixture reacts 12 hours at 110 DEG C, is cooled to
Room temperature, rotary evaporation removes water, post isolated target compound, productivity: 65%.1H NMR (500MHz, DMSO-d6)δ
8.06 (br s, 1H, NH), 7.81 (d, J=8.1Hz, 2H, ArH), 7.67 (d, J=8.1Hz, 2H, ArH), 7.48 (br s, 1H,
NH)；13C NMR (125MHz, DMSO-d6) δ 166.9,133.4,131.2,129.6,125.0.
Embodiment 4:3-trifluoromethyl benzamide
3-(trifluoromethyl)benzamide
By 3-trifluoromethylated benzaldehyde (87.1mg, 0.5mmol), oxammonium hydrochloride. (34.7mg, 0.5mmol), sodium carbonate
(26.5mg, 0.25mmol) and water (1ml) are sequentially added in 25ml Schlenk reaction bulb, after room temperature reaction half an hour, then add
Enter [Cp*Ir (H2O)3][OTf]2(10.2mg, 0.0150mmol, 3mol%) reactant mixture reacts 12 hours at 110 DEG C
After, it being cooled to room temperature, rotary evaporation removes water, post isolated target compound, productivity: 75%.
1H NMR (500MHz, DMSO-d6) δ 8.24 (br s, 1H, NH), 8.21 (s, 1H, ArH), 8.17 (d, J=7.8Hz,
1H, ArH), 7.90 (d, J=7.8Hz, 1H, ArH), 7.71 (t, J=7.8Hz, 1H, ArH), 7.64 (br s, 1H, NH)；13C NMR
(125MHz, DMSO-d6) δ 166.3,135.2,131.4,129.5,129.1 (q, JC-F=31.8Hz), 127.7 (q, JC-F=
2.8Hz), 124.1 (q, JC-F=270.8Hz), 124.0 (q, JC-F=2.8Hz).
Embodiment 5: Benzoylamide
benzamide
By benzaldehyde (53.1mg, 0.5mmol), oxammonium hydrochloride. (34.7mg, 0.5mmol), sodium carbonate (26.5mg,
0.25mmol) it is sequentially added in 25ml Schlenk reaction bulb with water (1ml), after room temperature reaction half an hour, adds [Cp*Ir
(H2O)3][OTf]2After (10.2mg, 0.0150mmol, 3mol%) reactant mixture reacts 12 hours at 110 DEG C, it is cooled to
Room temperature, rotary evaporation removes water, post isolated target compound, productivity: 68%.1H NMR (500MHz, CDCl3)δ7.82
(d, J=7.6Hz, 2H, ArH), 7.54 (t, J=7.3Hz, 1H, ArH), 7.45 (t, J=7.6Hz, 2H, ArH), 6.16 (br s,
1H, NH), 6.00 (br s, 1H, NH)；13C NMR (125MHz, CDCl3) δ 169.7,133.3,131.9,128.6,127.3.
Embodiment 6:4-methyl benzamide
4-methylbenzamide
By benzaldehyde (60.1mg, 0.5mmol), oxammonium hydrochloride. (34.7mg, 0.5mmol), sodium carbonate (26.5mg,
0.25mmol) it is sequentially added in 25ml Schlenk reaction bulb with water (1ml), after room temperature reaction half an hour, adds [Cp*Ir
(H2O)3][OTf]2After (10.2mg, 0.0150mmol, 3mol%) reactant mixture reacts 12 hours at 110 DEG C, it is cooled to
Room temperature, rotary evaporation removes water, post isolated target compound, productivity: 75%.1H NMR (500MHz, CDCl3)δ7.71
(d, J=7.9Hz, 2H, ArH), 7.25 (d, J=7.9Hz, 2H, ArH), 6.12 (br s, 1H, NH), 5.87 (br s, 1H, NH),
2.41 (s, 3H, CH3)；13C NMR (125MHz, CDCl3) δ 169.5,142.5,130.4,129.2,127.3,21.4.
Embodiment 7:3,4-dimethoxybenzarnide
3,4-dimethoxybenzamide
By Veratraldehyde oxime (83.1mg, 0.5mmol), [Cp*Ir (H2O)3][OTf]2(10.2mg,
0.0150mmol, 3mol%) and water (1ml) be sequentially added in 25ml Schlenk reaction bulb.Reactant mixture is anti-at 110 DEG C
After answering 12 hours, being cooled to room temperature, rotary evaporation removes water, post isolated target compound, productivity: 82%.1H NMR
(500MHz, CDCl3) δ 7.46 (d, J=1.9Hz, 2H, ArH), 7.34 (dd, J=8.3Hz and J=1.9Hz, 1H, ArH),
6.88 (d, J=8.4Hz, 1H, ArH), 6.09 (br s, 1H, NH), 5.84 (br s, 1H, NH), 3.94 (s, 3H, OCH3), 3.93
(s, 3H, OCH3)；13C NMR (125MHz, CDCl3) δ 169.2,152.1,148.9,125.8,120.1,110.7,110.2,
56.0.
Embodiment 8: phenyl acetamide
2-phenylacetamide
By hyacinthin (60.1mg, 0.5mmol), oxammonium hydrochloride. (34.7mg, 0.5mmol), sodium carbonate (26.5mg,
0.25mmol) it is sequentially added in 25ml Schlenk reaction bulb with water (1ml), after room temperature reaction half an hour, adds [Cp*Ir
(H2O)3][OTf]2(5.1mg, 0.0075mmol, 1.5mol%), after reactant mixture reacts 12 hours at 110 DEG C, cooling
To room temperature, rotary evaporation removes water, post isolated target compound, productivity: 86%.1H NMR (500MHz, CDCl3)δ
7.37 (t, J=7.4Hz, 2H, ArH), 7.32-7.26 (m, 3H, ArH), 5.47 (br s, 1H, NH), 5.37 (br s, 1H, NH),
3.60 (s, 2H, CH2)；13C NMR (125MHz, CDCl3) δ 173.6,134.8,129.4,129.0,127.4,43.3.
Embodiment 9: n-caproamide
hexanamide
Under nitrogen protection, by n-hexyl aldehyde (50.1mg, 0.5mmol), oxammonium hydrochloride. (34.7mg, 0.5mmol), sodium carbonate
(26.5mg, 0.25mmol) and water (1ml) are sequentially added in 25ml Schlenk reaction bulb, after room temperature reaction half an hour, then add
Enter [Cp*Ir (H2O)3][OTf]2(5.1mg, 0.0075mmol, 1.5mol%), reactant mixture reacts 12 hours at 110 DEG C
After, it being cooled to room temperature, rotary evaporation removes water, post isolated target compound, productivity: 71%.
1H NMR (500MHz, CDCl3) δ 5.41 (br s, 2H, NH), 2.22 (t, J=7.7Hz, 2H, CH2), 1.68-1.62
(m, 2H, CH2), 1.36-1.30 (m, 4H, CH2), 0.90 (t, J=6.9Hz, 3H, CH3)；13C NMR (125MHz, CDCl3)δ
176.0,35.9,31.3,25.2,22.3,13.9.
Embodiment 10: cinnamamide
cinnamamide
By cinnamic aldehyde (66.1mg, 0.5mmol), oxammonium hydrochloride. (34.7mg, 0.5mmol), sodium carbonate (26.5mg,
0.25mmol) it is sequentially added in 25ml Schlenk reaction bulb with water (1ml), after room temperature reaction half an hour, adds [Cp*Ir
(H2O)3][OTf]2(5.1mg, 0.0075mmol, 1.5mol%), after reactant mixture reacts 12 hours at 120 DEG C, cooling
To room temperature, rotary evaporation removes water, post isolated target compound, productivity: 84%.1H NMR (500MHz, DMSO-d6)δ
7.56-7.55 (m, 3H, ArH and NH), 7.43-7.36 (m, 4H, ArH), 7.13 (br s, 1H, NH), 6.61 (d, J=
16.0Hz, 1H, CH)；13C NMR (125MHz, DMSO-d6) δ 166.7,139.2,134.9,129.5,128.9,127.6,
122.3.
Embodiment 11:3-cinnamoyl chloride amine
(E)-3-(3-chlorophenyl)acrylamide
By 3-chlorocinnamaldehyde (83.3mg, 0.5mmol), oxammonium hydrochloride. (34.7mg, 0.5mmol), sodium carbonate (26.5mg,
0.25mmol) it is sequentially added in 25ml Schlenk reaction bulb with water (1ml), after room temperature reaction half an hour, adds [Cp*Ir
(H2O)3][OTf]2(5.1mg, 0.0075mmol, 1.5mol%), after reactant mixture reacts 12 hours at 120 DEG C, cooling
To room temperature, separating out crystal, sucking filtration obtains purpose product, productivity: 75%.
1H NMR (500MHz, CDCl3) δ 7.58 (d, J=15.8Hz, 1H, CH), 7.50 (s, 1H, ArH), 7.38-7.29
(m, 3H, ArH), 6.46 (d, J=15.7Hz, 1H, CH), 5.78 (br s, 2H, 2xNH)；13C NMR (125MHz, CDCl3)δ
168.0,140.7,136.3,134.7,130.0,129.7,127.4,126.2,121.2.
Embodiment 12:
Except using [Cp*Ir (H2O)3][BF4]2(4.6mg, 0.0075mmol, 1.5mol%) replaces [Cp*Ir (H2O)3]
[OTf]2, other reaction raw materials, condition and product are with embodiment 1, productivity: 75%
Embodiment 13:
Except using [Cp*Ir (H2O)3][PF6]2(5.1mg, 0.0075mmol, 1.5mol%) replaces [Cp*Ir (H2O)3]
[OTf]2(cat.3), other reaction raw materials, condition and product are with embodiment 1, productivity: 50%
Embodiment 14:
Except using [Cp*Ir (H2O)3][SO4 2-] (3.6mg, 0.0075mmol, 1.5mol%) replace [Cp*Ir (H2O)3]
[OTf]2, other reaction raw materials, condition and product are with embodiment 1, productivity: 10%
Embodiment 15:
Except [Cp*Ir (H2O)3][OTf]2(3.4mg, 0.005mmol, 1.0mol%), other reaction raw materials, condition and product
Thing is with embodiment 1, productivity: 65%
Embodiment 16:
Except [Cp*Ir (H2O)3][OTf]2(1.7mg, 0.0025mmol, 0.5mol%), other reaction raw materials, condition and product
Thing is with embodiment 1, productivity: 20%
Embodiment 17:
Except reaction temperature is 80 DEG C, other reaction raw materials, condition and product are with embodiment 1, productivity: 35%.
Embodiment 18:
Except reaction temperature is 100 DEG C, other reaction raw materials, condition and product are with embodiment 1, productivity: 65%.
Embodiment 19:
Except reaction temperature is 120 DEG C, other reaction raw materials, condition and product are with embodiment 1, productivity: 86%
Embodiment 20:
Except the response time is 8 hours, other reaction raw materials, condition and product are with embodiment 1, productivity: 60%.
Embodiment 21:
Except the response time is 4 hours, other reaction raw materials, condition and product are with embodiment 1, productivity: 30%.
Claims (7)
1. the method from aldehyde synthesizing amide, it is characterised in that described amide I
It passes through aldehyde II
With oxammonium hydrochloride. III
NH2OH.HCl
III
Reacting in the presence of water solublity iridium complex catalyst, wherein, R base is selected from aryl, single or multiple substituted aryl or fat
Fat base, n=0 or 1；Described water solublity iridium complex catalyst is [Cp*Ir (H2O)3][X]2, X=OTf, BF4、PF6, its knot
Structure formula is as follows:
X=OTf, BF4,PF6,；Its concrete synthesis step is as follows:
In reaction vessel, react under addition aldehyde, oxammonium hydrochloride., alkali and water, room temperature after being completely converted into oxime to aldehyde, add water-soluble
Property iridium complex, reactant mixture is cooled to room temperature after having reacted at 80-120 DEG C, select evaporation to remove water, and post separates
To target product.
Method from aldehyde synthesizing amide the most according to claim 1, it is characterised in that described R base selected from chlorophenyl,
Dichloro-phenyl, bromo phenyl, trifluoromethyl, phenyl, aminomethyl phenyl or methoxyphenyl.
Method from aldehyde synthesizing amide the most according to claim 1, it is characterised in that described R base is selected from benzyl or penta
Base.
Method from aldehyde synthesizing amide the most according to claim 1, it is characterised in that described catalyst amount relative to
The mol ratio of aldehyde is 0.5-3mol%.
Method from aldehyde synthesizing amide the most according to claim 1, it is characterised in that the described response time is 4～12 little
Time.
Method from aldehyde synthesizing amide the most according to claim 1, it is characterised in that described aldehyde rubs with oxammonium hydrochloride.
That ratio is 1:1.
Method from aldehyde synthesizing amide the most according to claim 1, it is characterised in that described alkali rubs with oxammonium hydrochloride.
That ratio is 1:2.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8044224B2 (en) * | 2007-01-29 | 2011-10-25 | Sumitomo Chemical Company, Limited | Chiral iridium aqua complex and method for producing optically active hydroxy compound by using the same |
| CN102424645A (en) * | 2011-07-29 | 2012-04-25 | 湖南大学 | Method for synthesizing aromatic amide and aromatic methanol |
| CN103172482A (en) * | 2013-01-16 | 2013-06-26 | 温州大学 | Method for preparing first-grade amide from aldoxime or formaldehyde and hydroxylamine |
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2013
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8044224B2 (en) * | 2007-01-29 | 2011-10-25 | Sumitomo Chemical Company, Limited | Chiral iridium aqua complex and method for producing optically active hydroxy compound by using the same |
| CN102424645A (en) * | 2011-07-29 | 2012-04-25 | 湖南大学 | Method for synthesizing aromatic amide and aromatic methanol |
| CN103172482A (en) * | 2013-01-16 | 2013-06-26 | 温州大学 | Method for preparing first-grade amide from aldoxime or formaldehyde and hydroxylamine |
Non-Patent Citations (1)
| Title |
|---|
| Nathan A. Owston等.Iridium-Catalyzed Conversion of Alcohols into Amides via Oximes.《Org. Lett》.2006,第9卷(第1期),Supporting information 第3页第1-2段及第4页第1段. * |
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