1,3-dimethyl-7-nitroquinolin-4(1H)-one → 5-amino-1,3-dimethylquinolin-4(1H)-one

HRID 1948102Notes

Reaction equation

HRID 1948102 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[C:7]([N+:12]([O-])=O)[CH:8]=[CH:9][CH:10]=2)[C:5](=[O:15])[C:4]([CH3:16])=[CH:3]1.CN1C2C(=CC=C([N+]([O-])=O)C=2)C(=O)C(C)=C1.[H][H]>CO.[Pd]>[NH2:12][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[C:5](=[O:15])[C:4]([CH3:16])=[CH:3][N:2]2[CH3:1]

Participants

6

Reactant 3

HCID 672544121,3-dimethyl-7-nitroquinolin-4(1H)-oneHCID 672547551,3-dimethyl-5-nitroquinolin-4(1H)-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 672550595-amino-1,3-dimethylquinolin-4(1H)-oneYield 28%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1,3-dimethyl-5-nitroquinolin-4(1H)-one and 1,3-dimethyl-7-nitroquinolin-4(1H)-one Compound 299B, 2.2 g, 10 mmol) in MeOH (150 mL) was hydrogenated over 5% Pd/C (0.8 g) at 40° C. under 40 psi hydrogen pressure overnight. The catalyst was filtered off and the filtrate was concentrated and purified by HPLC to give the title compound (540 mg, 28%) as a pure regioisomer. 1H NMR (DMSO-d6, 400 MHz): δ=1.92 (s, 3H), 3.69 (s, 3H), 6.63 (d, J=8.0 Hz, 1H), 6.80 (d, J=8.4 Hz, 1H), 7.40 (t, J=8.0 Hz, 1H), 7.91 (s, 1H).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated
  3. custompurified by HPLC

Sources & evidence

ORD record
ord-cb60829637ef4d20bf5688593323c665
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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