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

HRID 1840399Notes

Reaction equation

HRID 1840399 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 (ppt) was collected with suction. The ppt was washed with toluene and dichloromethane and dried under reduced pressure to give a brown powder (21.6 g). ESI−MS: m/z 297 (MH+); 1H-NMR (DMSO-d6): δ3.74 (3H, s), 6.54 (1H, dd, J=8.5 Hz, J=2.5 Hz), 7.00 (1H, bd, J=8.5 Hz), 7.17 (1H, t, J=8.5 Hz), 7.42 (1H, t-like, J=ca 2.5 Hz), 7.73 (1H, d, 5 Hz), 8.71 (1H, s), 8.91 (1H, d, J=5 Hz), 10.65 (1H, brs).

Workup

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

Sources & evidence

ORD record
ord-9cadb365498c43608f219ecb7564a858
Source dataset
uspto-grants-2004_01
Patent number
US06680326B2

Reaction notes

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