Ammonium Hydroxide → 3-Amino-6-(3,4-dimethoxyphenyl)pyridine-2-carbonitrile

HRID 1517397Notes

Reaction equation

HRID 1517397 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[N:16]=[C:15]([C:17]#[N:18])[C:14]([N+:19]([O-])=O)=[CH:13][CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[OH-].[NH4+]>CO.Cl.[Fe]>[NH2:19][C:14]1[C:15]([C:17]#[N:18])=[N:16][C:11]([C:5]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)=[CH:12][CH:13]=1

Participants

6

Reactant 2

HCID 14923Ammonium HydroxideHCID 688404046-(3,4-Dimethoxyphenyl)-3-nitropyridine-2-carbonitrile

Product 1

HCID 688439043-Amino-6-(3,4-dimethoxyphenyl)pyridine-2-carbonitrileYield 64.1%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

Iron (7.14 g, 128 mmol) was added portion wise to a stirred suspension of 6-(3,4-dimethoxyphenyl)-3-nitropyridine-2-carbonitrile (4.56 g; 16 mmol) in methanol (80 ml) and 37% HCl (25 ml). The mixture was refluxed for 5 hours and, after cooling, the pH was adjusted to 9-10 by means of concentrated ammonium hydroxide (30 ml). The mixture was filtered over Celite and washed with MeOH and EtOAc. The filtrate was evaporated to dryness and the residue was purified on silica gel column chromatography, using a mixture of CH2Cl2/EtOAc (in a ratio of 95:5) as eluent, to obtain the pure title compound (2.62 g, yield 64%) which was characterized by its mass spectrum as follows: MS (m/z): 256 ([M+H]+, 100).

Workup

  1. temperatureThe mixture was refluxed for 5 hours
  2. temperatureafter cooling
  3. filtrationThe mixture was filtered over Celite
  4. washwashed with MeOH and EtOAc
  5. customThe filtrate was evaporated to dryness
  6. customthe residue was purified on silica gel column chromatography
  7. additiona mixture of CH2Cl2/EtOAc (in a ratio of 95:5) as eluent

Sources & evidence

ORD record
ord-db0f78fec4614311a8de4c1b4cce0a7c
Source dataset
uspto-grants-2012_07
Patent number
US08232278B2

Reaction notes

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