3-Chloroaniline → 5,7-dioxo-6,7-dihydro-5H-[2]pyrindine-6-carboxylic acid (3-chlorophenyl)-amide
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.[Cl:17][C:18]1[CH:19]=[C:20]([NH2:24])[CH:21]=[CH:22][CH:23]=1>>[Cl:17][C:18]1[CH:19]=[C:20]([NH:24][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:21]=[CH:22][CH:23]=1Participants
3
Procedure
In a similar manner to Example 1a, 5,7-dioxo-6,7-dihydro-5H-[2]pyrindine-6-carboxylic acid (3-chloro-phenyl)-amide was obtained starting from 5,7-dioxo-6,7-dihydro-5H-[2]pyrindine-6-carboxylic acid ethyl ester and 3-chloro-phenylamine. The desired product was obtained as a brownish orange powder. ESI−MS: m/z 301 (MH+); 1H-NMR (DMSO-d6): δ6.96-7.00 (1H, m), 7.27-7.29 (2H, m), 7.35 (1H, dd, J=1.3 Hz, 4.6 Hz), 7.98-7.99 (1H, m), 8.53 (1H, d, J=1.0 Hz), 8.74 (1H, d, J=4.6 Hz), 10.92 (1H, brs).
Sources & evidence
- ORD record
- ord-16aa91cf14ad43d79cd0291929972f1a
- Source dataset
- uspto-grants-2004_01
- Patent number
- US06680326B2
Reaction notes
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