Hydrochloric Acid → 6-Chloro-5-fluoroindolin-2-one

HRID 248429

반응식

HRID 248429 반응식
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([F:9])=[CH:4][C:3]=1[CH2:10][C:11]([O:13]C)=O.O.Cl>C(Cl)Cl.C(O)(=O)C>[F:9][C:5]1[CH:4]=[C:3]2[C:2](=[CH:7][C:6]=1[Cl:8])[NH:1][C:11](=[O:13])[CH2:10]2

참가 물질

6

반응물 3

HCID 313Hydrochloric Acid3회HCID 962WaterHCID 10900080Methyl (2-amino-4-chloro-5-fluorophenyl)acetate2회

생성물 1

HCID 97940836-Chloro-5-fluoroindolin-2-one

시약·촉매·용매 2

HCID 176Acetic Acid용매3회HCID 6344Dichloromethane용매2회

실험 절차

Compound (III) is obtained by cyclizing (II) with an acid as shown in step [b] of Scheme 1. Compound (II) is dissolved in a mixture of an acid and a cosolvent, preferably the acid is glacial acetic acid in which instance the preferred cosolvent is water or the acid is hydrochloric acid in which instance the preferred cosolvent is methylene chloride. With acetic acid the ratio of the acid and cosolvent mixture ranges from 2:1 to pure acetic acid respectively, the preferred ratio being 6:1. With HCl, much less acid is required, preferably 1:4 3N HCl to CH2Cl2. Once compound (II) is dissolved, the reaction mixture is stirred at ambient temperature for from 6 to 7 hours to produce 5-fluoro-6-chlorooxindole (III). Compound (III) is readily purified by recrystallization from ethyl acetate to yield an off-white solid.

출처 및 근거

ORD 기록
ord-e96b6c2225c34fcbb498b079655072ef
출처 데이터셋
uspto-grants-1993_05
특허 번호
US05210212

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