Chloroacetonitrile → 6-Methyl-2-(3-nitrophenylamino)nicotinic acid cyanomethyl ester

HRID 478720Notes

Reaction equation

HRID 478720 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[N:3]=1.[CH2:21]([N:23](CC)CC)[CH3:22].ClCC#N>CC(C)=O>[C:21]([CH2:22][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([CH3:1])=[N:3][C:4]=1[NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=1)#[N:23]

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 8471TriethylamineHCID 180026426-Methyl-2-(3-nitrophenylamino)nicotinic acid

Product 1

HCID 698502536-Methyl-2-(3-nitrophenylamino)nicotinic acid cyanomethyl esterYield 90%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a suspension of 6-methyl-2-(3-nitrophenylamino)-nicotinic acid (15.06 g, 55.11 mmol) in acetone (220ml) was added triethylamine (6.13 g, 60.6 mmol) and chloroacetonitrile (4.58 g, 60.6 mmol), and the mixture was heated under reflux overnight. The reaction mixture was filtered to remove an insoluble. The filtrate was evaporated. The resultant residue was washed successively with 1N aqueous sodium hydroxide and water, and dried to give 6-methyl-2-(3-nitrophenylamino)nicotinic acid cyanomethyl ester (15.44 g, 90%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight
  3. filtrationThe reaction mixture was filtered
  4. customto remove an insoluble
  5. customThe filtrate was evaporated
  6. washThe resultant residue was washed successively with 1N aqueous sodium hydroxide and water
  7. customdried

Sources & evidence

ORD record
ord-12f05baa64a444bbafc8d638d7a1bba7
Source dataset
uspto-grants-2003_11
Patent number
US06642250B2

Reaction notes

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