Triethylamine → 6-Methyl-2-(3-nitrophenylamino)nicotinic acid methyl ester

HRID 478721Notes

Reaction equation

HRID 478721 reaction equation
C([CH2:3][O:4][C:5](=[O:23])[C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[N:8][C:7]=1[NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=1)#N.C(N(CC)CC)C>CO>[CH3:3][O:4][C:5](=[O:23])[C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[N:8][C:7]=1[NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 698502536-Methyl-2-(3-nitrophenylamino)nicotinic acid cyanomethyl ester

Product 1

HCID 698496966-Methyl-2-(3-nitrophenylamino)nicotinic acid methyl esterYield 97.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 6-methyl-2-(3-nitrophenylamino)nicotinic acid cyanomethyl ester (15.44 g, 49.43 mmol) and triethylamine (1.00 g, 9.89 mmol) in dry methanol (160 ml) was heated under reflux overnight. After cooling, crystals were collected by filtration, washed with methanol, and dried to give 6-methyl-2-(3-nitrophenylamino)nicotinic acid methyl ester (13.84 g, 97%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. temperatureAfter cooling
  4. filtrationcrystals were collected by filtration
  5. washwashed with methanol
  6. customdried

Sources & evidence

ORD record
ord-13e780f0f6804b45a8771ac4c347675a
Source dataset
uspto-grants-2003_11
Patent number
US06642250B2

Reaction notes

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