Methyl 3-(4-carboxy-2-nitrophenyl)propionate → 2-Oxo-1,2,3,4-tetrahydroquinoline-7-carboxylic acid

HRID 483156Notes

Reaction equation

HRID 483156 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12](OC)=[O:13])=[C:6]([N+:16]([O-])=O)[CH:5]=1)([OH:3])=[O:2].CO.[OH-].[Na+]>[Pd].CO>[C:1]([C:4]1[CH:5]=[C:6]2[C:7]([CH2:10][CH2:11][C:12](=[O:13])[NH:16]2)=[CH:8][CH:9]=1)([OH:3])=[O:2]

Participants

5

Reactant 2

HCID 13242991Methyl 3-(4-carboxy-2-nitrophenyl)propionateHCID 23721981Sodium hydroxide methanol

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5 Grams of methyl 3-(4-carboxy-2nitrophenyl)propionate, 8.87 ml of 2.226N-sodium hydroxide methanol solution, 100 ml of methanol and 1 g of 5%-Pd-C (50% in water) were well mixed together and this mixture was catalytically reduced at a normal temperature under a normal pressure. Then the catalyst was removed from the reaction mixture by filtration, and the pH of the filtrate was adjusted to about pH=1 by adding concentrated hydrochloric acid. The precipitated crystals were collected by filtration and recrystallized from methanol to obtain 3.62 g of 7-carboxy-3,4-dihydrocarbostyril in the form of colorless needle-like crystals.

Workup

  1. customThen the catalyst was removed from the reaction mixture by filtration
  2. additionby adding concentrated hydrochloric acid
  3. filtrationThe precipitated crystals were collected by filtration
  4. customrecrystallized from methanol

Sources & evidence

ORD record
ord-8e91a94a28ed4996845a61f87292fe71
Source dataset
uspto-grants-1986_03
Patent number
US04578381

Reaction notes

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