1-Naphthylamine → 5,7-dioxo-6,7-dihydro-5H-[2]pyrindine-6-carboxylic acid naphthalen-1-ylamide
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.[C:17]1([NH2:27])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1>>[C:17]1([NH:27][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])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1Participants
3
Procedure
In a similar manner to Example 1a, 5,7-dioxo-6,7-dihydro-5H-[2]pyrindine-6-carboxylic acid naphthalen-1-ylamide was obtained starting from 5,7-Dioxo-6,7-dihydro-5H-[2]pyrindine-6-carboxylic acid ethyl ester and naphthalen-1-ylamine. The desired product was obtained as a light brownish powder. ESI−MS: m/z 317 (MH+); 1H-NMR (DMSO-d6): δ7.38-7.67 (5H, m), 7.91 (1H, d, J=8.1 Hz), 8.38 (1H, d, J=8.7 Hz), 8.54 (1H, dd, J=1.1 Hz, 7.6 Hz), 8.57 (1H, d, J=1.1 Hz), 8.75 (1H, d, J=4.9 Hz), 11.61 (1H, brs).
Sources & evidence
- ORD record
- ord-93841ccfc003428f8aa3e067bccd71c9
- Source dataset
- uspto-grants-2004_01
- Patent number
- US06680326B2
Reaction notes
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