Acetic Acid → 5,7-dioxo-6,7-dihydro-5H-[2]pyrindine-6-carboxylic acid (3-methoxy-4-methyl-phenyl)-amide

HRID 1840406Notes

Reaction equation

HRID 1840406 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.CO[C:19]1[C:20](C)=[C:21]([NH2:25])C=[CH:23][CH:24]=1.[C:27]([OH:30])(=O)[CH3:28].[C:31]1(C)C=CC=CC=1>>[CH3:31][O:30][C:27]1[CH:28]=[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:20]=[CH:19][C:24]=1[CH3:23]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 1140TolueneHCID 111486955,7-Dioxo-6,7-dihydro-5H-[2]pyrindine-6-carboxylic acid ethyl esterHCID 118048223-Methoxy-2-methylaniline

Product 1

HCID 1317243075,7-dioxo-6,7-dihydro-5H-[2]pyrindine-6-carboxylic acid (3-methoxy-4-methyl-phenyl)-amide

Procedure

5,7-Dioxo-6,7-dihydro-5H-[2]pyrindine-6-carboxylic acid ethyl ester (975 mg) (see Robin D. Allan and Joyce Fong, Aust. J. Chem., Vol. 36, Pp. 1221-1226,1983), 3-metoxy-2-methyl-phenylamine (750 mg) and acetic acid (0.4 ml) were suspended in toluene (30 ml). This mixture was refluxed for one hour under nitrogen. The mixture was cooled to room temperature and the ppt was collected with suction. The ppt was washed with toluene and dichloromethane and dried under reduced pressure to give an orange powder (1.1 g). ESI−MS: m/z 311 (MH+); 1H-NMR (DMSO-d6+triethylamine (1 eq.)): δ2.18 (3H, s), 3.77 (3H, s), 6.60 (1H, d, J=8 Hz), 7.05 (1H, t, J=8 Hz), 7.32 (1H, dd, J=4.5 Hz, J=1 Hz), 7.99 (1H, d, J=8 Hz), 8.50 (1H, d, J=1 Hz), 8.71 (1H, d, J=4.5 Hz), 10.6 (1H, s).

Workup

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

Sources & evidence

ORD record
ord-1733f9d508104059ae9d631fcaa9376f
Source dataset
uspto-grants-2004_01
Patent number
US06680326B2

Reaction notes

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