HCID 820544, compound → HCID 20240340, compound
Reaction equation
[OH:1][C:2]1[C:11]([CH3:12])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[N:7][CH:8]=2)[N:3]=1.N1C=CC(NC(=O)C(C)=C)=CC=1>>[CH3:12][CH:11]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[N:7][CH:8]=2)[NH:3][C:2]1=[O:1]Participants
Procedure
2-Hydroxy-3-methyl-1,6-naphthyridine, the tautomeric form of 3-methyl-1,6-naphthyridin-2(1H)-one, was reportedly prepared by Ogata et al. [Chem. Pharm. Bull. 20, 2264 (1972)] in two steps by first photocyclization of N-(4-pyridinyl)methacrylamide to produce 1,2,3,4-tetrahydro-3-methyl-2-oxo-1,6-naphthyridine and then dehydrogenating said tetrahydro compound by heating it in acetic acid. 3-Cyano-2-hydroxy-1,6-naphthyridine, the tautomeric form of 3-cyano-1,6-naphthyridin-2(1H)-one, was reportedly prepared by Hawes et al [J. Med. Chem. 16, 849 (1973)] by refluxing 4-aminonicotinaldehyde and ethyl cyanoacetate in ethanol in the presence of piperidine. The compound was reportedly used as an intermediate for preparing 2-amino-3-cyano-1,6-naphthyridine, a "potential diuretic agent", and is shown as having low diuretic activity.
Sources & evidence
- ORD record
- ord-33650c05077b4c128e803a6782848ab4
- Source dataset
- uspto-grants-1983_11
- Patent number
- US04415580
Reaction notes
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