Sulfuric Acid → 2-(2-oxo-1,2-dihydroquinolin-4-yl)acetic acid

HRID 703442Notes

Reaction equation

HRID 703442 reaction equation
C(O[C:5]([CH2:10][C:11](=[O:19])[NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[CH:6][C:7]([OH:9])=[O:8])(=O)C.S(=O)(=O)(O)O>O>[O:19]=[C:11]1[CH:10]=[C:5]([CH2:6][C:7]([OH:9])=[O:8])[C:14]2[C:13](=[CH:18][CH:17]=[CH:16][CH:15]=2)[NH:12]1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 541950343-Acetyloxy-5-oxo-5-phenylamino-2-pentenoic acid

Product 1

HCID 47377352-(2-oxo-1,2-dihydroquinolin-4-yl)acetic acidYield 52.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

150 g (0.57 mol) of 3-acetyloxy-5-oxo-5-phenylamino-2-pentenoic acid are poured in small portions while stirring into 500 ml of 95-97% sulphuric acid, and the reaction medium is then heated to 100° C. for 2 h. After being cooled, this solution is poured into a mixture of 1 kg of ice and 500 ml of water while stirring. The solid thereby obtained is drained. It is washed with 3 times 100 ml of water and dried for 8 h at 60° C. 60.5 g (52%) of 2-oxo-1,2-dihydro-4-quinolineacetic acid, melting point 213°-215° C., are obtained.

Workup

  1. temperatureAfter being cooled
  2. customThe solid thereby obtained
  3. washIt is washed with 3 times 100 ml of water
  4. customdried for 8 h at 60° C

Sources & evidence

ORD record
ord-5dcc0b84346c4ec9880956a1e7b30d54
Source dataset
uspto-grants-1991_01
Patent number
US04983607

Reaction notes

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