3-methyl-5-nitroquinolin-4(1H)-one → 5-amino-3-methylquinolin-4(1H)-one

HRID 1948006Notes

Reaction equation

HRID 1948006 reaction equation
NC1C=CC(F)=CC=1C(NC)=O.[CH3:13][C:14]1[C:23](=[O:24])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][C:21]=2[N+:25]([O-])=O)[NH:16][CH:15]=1>>[NH2:25][C:21]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:22]=1[C:23](=[O:24])[C:14]([CH3:13])=[CH:15][NH:16]2

Participants

3

Reactant 2

HCID 105123693-methyl-5-nitroquinolin-4(1H)-oneHCID 431325582-Amino-5-fluoro-N-methylbenzamide2×

Product 1

HCID 672540655-amino-3-methylquinolin-4(1H)-one

Procedure

The title compound was prepared according to procedure for 2-Amino-5-fluoro-N-methylbenzamide (Compound 102A) using 3-methyl-5-nitroquinolin-4(1H)-one (Eur J Med Chem. 1992, 37, 547-570). 1H NMR (DMSO-d6, 400 MHz): δ=1.87 (d, J=0.76 Hz, 3H), 6.21 (dd, J=7.83, 1.01 Hz, 1H), 6.40 (dd, J=8.08, 1.01 Hz, 1H), 7.12 (t, J=8.08 Hz, 1H), 7.62 (dd, J=5.94, 0.88 Hz, 1H), 11.19 (d, J=5.05 Hz, 1H). MS (ES+): m/z 175.07 [MH+] (TOF, polar).

Sources & evidence

ORD record
ord-21de7bc858ae45e69517051092834130
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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