Acetic Acid → 2-[(1-Cyano-1,2-dimethylpropyl)aminocarbonyl]nicotinic acid

HRID 2231368Notes

Reaction equation

HRID 2231368 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]2[C:7]([O:9][C:10](=[O:11])[C:2]=12)=[O:8].[C:12](O)(=O)C.[C:16]([C:19]1[N:27]=CC=[CH:24][C:20]=1[C:21](O)=O)(=O)[NH2:17]>C1(C)C=CC=CC=1>[C:16]([C:19]([NH:27][C:10]([C:2]1[N:1]=[CH:6][CH:5]=[CH:4][C:3]=1[C:7]([OH:9])=[O:8])=[O:11])([CH3:12])[CH:20]([CH3:24])[CH3:21])#[N:17]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 69688Furo[3,4-b]pyridine-5,7-dioneHCID 2588102-Carbamoylpyridine-3-carboxylic acid

Product 1

HCID 135636102-[(1-Cyano-1,2-dimethylpropyl)aminocarbonyl]nicotinic acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The aminonitrile (1.108 mol) is added over a ten minute period to a stirred solution of 2,3-pyridinedicarboxylic anhydride (1.0 mol) containing acetic acid (2.0 mol) in toluene, while maintaining the temperature of the reaction mixture below 25° C. Upon completion of the aminonitrile addition the reaction mixture is stirred for one and one-half hrs and then weighed and analyzed by high performance liquid chromatography for the desired 2-carbamoyl nicotinic acid.

Workup

  1. temperaturewhile maintaining the temperature of the reaction mixture below 25° C

Sources & evidence

ORD record
ord-9aee0ee399a14317a1eadad5ebbdcc36
Source dataset
uspto-grants-1988_11
Patent number
US04782157

Reaction notes

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