Aniline → alpha-Hydroxyacetophenone

HRID 2072243Notes

Reaction equation

HRID 2072243 reaction equation
N[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:8](Cl)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:17]([NH:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(Cl)(=N)C1C=CC=CC=1>>[OH:24][CH2:17][C:8]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:15].[C:26]1([N:25]=[C:17]([O:24][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[C:8](=[O:15])[CH3:9])[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 6115AnilineHCID 7168BenzanilideHCID 7412Benzoyl chlorideHCID 12823444HCID 12823444, compound

Product 2

HCID 68490alpha-HydroxyacetophenoneHCID 4070889HCID 4070889, compound

Procedure

In a third method the 1,2-diphenylquinolones (IV, m = O) are prepared by acylation of an appropriate aniline with an appropriate benzoyl chloride, chlorination of the resulting benzanilide, reaction of the benzimidoyl chloride so obtained with an appropriate 2-hydroxyacetophenone and rearrangement of the resulting 2-acetylphenyl N-phenylbenzimidate. The sequence of reactions is illustrated by the following equations: ##STR9##

Sources & evidence

ORD record
ord-31742658061b4ccdad60332a9b402ebf
Source dataset
uspto-grants-1977_09
Patent number
US04049715

Reaction notes

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