2-(4-tert-Butoxycarbonyl-2-nitro-benzylidene)-succinic Acid Dimethyl Ester → 3-Methoxycarbonylmethyl-2-oxo-1,2,3,4-tetrahydro-quinoline-7-carboxylic acid tert-butyl ester

HRID 2302005Notes

Reaction equation

HRID 2302005 reaction equation
C[O:2][C:3](=O)[C:4](=[CH:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:13][C:12]=1[N+:24]([O-])=O)[CH2:5][C:6]([O:8][CH3:9])=[O:7]>CO.[Pd]>[C:20]([O:19][C:17]([C:14]1[CH:13]=[C:12]2[C:11]([CH2:10][CH:4]([CH2:5][C:6]([O:8][CH3:9])=[O:7])[C:3](=[O:2])[NH:24]2)=[CH:16][CH:15]=1)=[O:18])([CH3:23])([CH3:22])[CH3:21]

Participants

4

Reactant 1

HCID 699780382-(4-tert-Butoxycarbonyl-2-nitro-benzylidene)-succinic Acid Dimethyl Ester

Product 1

HCID 699798593-Methoxycarbonylmethyl-2-oxo-1,2,3,4-tetrahydro-quinoline-7-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-(4-tert-butoxycarbonyl-2-nitro-benzylidene)-succinic acid dimethyl ester (5.0 g, 13.2 mmol) in methanol (40 mL) with 10% Pd/C was hydrogenated at 50 psi and 25° C. for 20 h. The reaction mixture was filtered to afford after evaporation in vacuo the title compound as a gray solid (3.56 g, 85%). NMR (dmso-d6, 200 MHz) : δ1.5 (s, 9H, tert-butyl), 2.7-3.4 (m, 5H, CH2CHCH2), 3.6 (s, 3H, CH3), 7.2-7.5 (m, 3H, ArH), 10.3 (s, 1H, NH).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto afford
  3. customafter evaporation in vacuo the title compound as a gray solid (3.56 g, 85%)

Sources & evidence

ORD record
ord-a64b3117d58347aaa0e437cc413d03f1
Source dataset
uspto-grants-2002_08
Patent number
US06429214B1

Reaction notes

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