Acetic Acid → 5,7-dioxo-6,7-dihydro-5H-[2]pyrindine-6-carboxylic acid (3-methoxy-phenyl)-amide

HRID 496736Notes

Reaction equation

HRID 496736 reaction equation
C(O[C:4]([CH:6]1[C:14](=[O:15])[C:13]2[CH:12]=[N:11][CH:10]=[CH:9][C:8]=2[C:7]1=[O:16])=[O:5])C.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([NH2:25])[CH:20]=1.C(O)(=O)C>C1(C)C=CC=CC=1>[CH3:17][O:18][C:19]1[CH:20]=[C:21]([NH:25][C:4]([CH:6]2[C:14](=[O:15])[C:13]3[CH:12]=[N:11][CH:10]=[CH:9][C:8]=3[C:7]2=[O:16])=[O:5])[CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 108243-MethoxyanilineHCID 111486955,7-Dioxo-6,7-dihydro-5H-[2]pyrindine-6-carboxylic acid ethyl ester

Product 1

HCID 114833205,7-dioxo-6,7-dihydro-5H-[2]pyrindine-6-carboxylic acid (3-methoxy-phenyl)-amide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5,7-Dioxo-6,7-dihydro-5H-[2]pyrindine-6-carboxylic acid ethyl ester (18 g) (see, Robin D. Allan and Joyce Fong, Aust. J. Chem., Vol. 36, pp. 1221-1226, 1983), m-anisidine (17.7 ml) and acetic acid (9 ml) were suspended in toluene (1,000 ml). This mixture was refluxed for 110 minutes under nitrogen. The mixture was cooled to room temperature and the precipitate was collected with suction. The precipitate was washed with toluene and dichloromethane and dried under reduced pressure to give a brown powder (21.6 g).

Workup

  1. temperatureThis mixture was refluxed for 110 minutes under nitrogen
  2. customthe precipitate was collected with suction
  3. washThe precipitate was washed with toluene and dichloromethane
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-7dd87b0bccb84839a980cf9196ae89b7
Source dataset
uspto-grants-2005_09
Patent number
US06946472B2

Reaction notes

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