4-(3-Ethoxy-3-oxoprop-1-enyl)-3-nitrobenzoic acid → 2-Oxo-1,2,3,4-tetrahydroquinoline-7-carboxylic acid

HRID 887077Notes

Reaction equation

HRID 887077 reaction equation
C([O:3][C:4](=O)[CH:5]=[CH:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][C:8]=1[N+:16]([O-])=O)C>CO.[Pd]>[O:3]=[C:4]1[CH2:5][CH2:6][C:7]2[C:8](=[CH:9][C:10]([C:11]([OH:13])=[O:12])=[CH:14][CH:15]=2)[NH:16]1

Participants

4

Reactant 1

HCID 685356704-(3-Ethoxy-3-oxoprop-1-enyl)-3-nitrobenzoic acid

Product 1

HCID 132430012-Oxo-1,2,3,4-tetrahydroquinoline-7-carboxylic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To 10% Pd—C (100 mg) under nitrogen atmosphere was added a solution of 4-(3-ethoxy-3-oxoprop-1-enyl)-3-nitrobenzoic acid (45) (29 g, 0.11 mol) in 75 mL methanol and kept at 50 psi H2 atmosphere for 12 h. The reaction mixture was filtered through a sintered funnel and the filtrate was concentrated to give the pure compound 22. Off-white solid (20.9 g, 96%). 1H NMR (400 MHz, CDCl3): δ 2.44 (t, J=6.8 Hz, 2H); 2.90 (t, J=6.8 Hz, 2H); 7.25 (d, J=7.6 Hz, 1H); 7.44 (s, 1H); 7.47 (dd, J=7.6, 1.6 Hz, 1H); 10.22 (broad s, 1H); 12.85 (broad s, 1H). 13C NMR (75 MHz, CDCl3): δ 24.8, 30.0, 115.1, 123.5, 127.8, 127.9, 129.0, 139.0, 167.5, 169.0.

Workup

  1. filtrationThe reaction mixture was filtered through a sintered funnel
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-a41d8f2223ae4dd488696d698c73a2c3
Source dataset
uspto-grants-2012_08
Patent number
US08247420B2

Reaction notes

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