Sodium hydride → 4-Hydroxy-3-(2-methylphenyl)quinolin-2(1H)-one

HRID 364923Notes

Reaction equation

HRID 364923 reaction equation
[C:1]1([CH3:21])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]([NH:10][C:11]1[C:12](=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:13]([O:15]C)=O)=[O:9].[H-].[Na+]>C1(C)C=CC=CC=1>[OH:15][C:13]1[C:12]2[C:11](=[CH:20][CH:19]=[CH:18][CH:17]=2)[NH:10][C:8](=[O:9])[C:7]=1[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[CH3:21]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 6464972Benzoic acid, 2-[[(2-methylphenyl)acetyl]amino]-, methyl ester

Product 1

HCID 547320144-Hydroxy-3-(2-methylphenyl)quinolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of methyl N-(o-tolylacetyl)anthranilate (2.8 g.) and sodium hydride (1.1 g. of a 50% w/w dispersion in mineral oil) in toluene (50ml.) was heated at 100° for 1 hr. The reaction mixture was cooled and extracted with water (2×50 ml.). The aqueous extract was acidified to pH 2. The solid which precipitated was filtered off, stirred together with hot ethanol (25 ml.), and the mixture filtered to give 4-hydroxy-3-o-tolylquinolin-2-one, m.p. over 300°.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with water (2×50 ml.)
  3. extractionThe aqueous extract
  4. customThe solid which precipitated
  5. filtrationwas filtered off
  6. filtrationthe mixture filtered

Sources & evidence

ORD record
ord-9c1d8304016440359b56117e12bebb5f
Source dataset
uspto-grants-1986_08
Patent number
US04607039

Reaction notes

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