Acetic Anhydride → [(E)-[(3-chloro-2-hydroxy-4-methoxyphenyl)-(2-fluorophenyl)methylidene]amino] acetate

HRID 652899Notes

Reaction equation

HRID 652899 reaction equation
[Cl:1][C:2]1[C:3]([OH:20])=[C:4]([CH:15]=[CH:16][C:17]=1[O:18][CH3:19])/[C:5](=[N:13]\[OH:14])/[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[F:12].[C:21](OC(=O)C)(=[O:23])[CH3:22].C([O-])(O)=O.[Na+]>CCOCC>[C:21]([O:14]/[N:13]=[C:5](/[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[F:12])\[C:4]1[CH:15]=[CH:16][C:17]([O:18][CH3:19])=[C:2]([Cl:1])[C:3]=1[OH:20])(=[O:23])[CH3:22]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 1364774092-chloro-6-[(E)-C-(2-fluorophenyl)-N-hydroxycarbonimidoyl]-3-methoxyphenol

Product 1

HCID 136477412[(E)-[(3-chloro-2-hydroxy-4-methoxyphenyl)-(2-fluorophenyl)methylidene]amino] acetate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

E-3-chloro-2'-fluoro-2-hydroxy4-methoxybenzophenone oxime (18.1 g) is warmed at 60° C. for 30 minutes with 9 ml of acetic anhydride. The reaction mixture is distributed between ether and 10% NaHCO3 and washed with 10% NaHCO3 until the washes remained basic. Drying, evaporation and trituration with hexane gives E-3-chloro-2'-fluoro-2-hydroxy-4-methoxybenzophenone O-acetyl oxime, mp 125°-128° C.

Workup

  1. washwashed with 10% NaHCO3 until the washes
  2. customDrying
  3. customevaporation and trituration with hexane

Sources & evidence

ORD record
ord-bc6078ebe0154a9ebaf727b038c1eb99
Source dataset
uspto-grants-1987_06
Patent number
US04673746

Reaction notes

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