Aniline → 5,7-dioxo-6,7-dihydro-5H-[2]pyrindine-6-carboxylic acid phenylamide
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.[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[C:18]1([NH:17][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:23]=[CH:22][CH:21]=[CH:20][CH:19]=1Participants
3
Procedure
In a similar manner to Example 1a, 5,7-dioxo-6,7-dihydro-5H-[2]pyrindine-6-carboxylic acid phenylamide was obtained starting from 5,7-dioxo-6,7-dihydro-5H-[2]pyrindine-6-carboxylic acid ethyl ester and aniline. The desired product was obtained as a brownish orange powder. ESI−MS: m/z 267 (MH+); 1H-NMR (DMSO-d6): δ6.93 (1H, t, J=7.3 Hz), 7.26 (2H, t-like, 7.3 Hz), 7.33 (1H, dd, J=1.4 Hz, 4.6 Hz), 7.59 (2H, d, J=7.3 Hz), 8.51 (1H, d, J=1.4 Hz), 8.72 (1H, d, J=4.6 Hz), 10.78 (1H, brs).
Sources & evidence
- ORD record
- ord-2823ec39d5254e1e9112b79674fdd906
- Source dataset
- uspto-grants-2004_01
- Patent number
- US06680326B2
Reaction notes
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