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

HRID 248429

反応式

HRID 248429 の反応式
[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

参加物

6

反応物 3

HCID 313Hydrochloric Acid3 回HCID 962WaterHCID 10900080Methyl (2-amino-4-chloro-5-fluorophenyl)acetate2 回

生成物 1

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

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒3 回HCID 6344Dichloromethane溶媒2 回

実験手順

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.

出典と根拠

ORDレコード
ord-e96b6c2225c34fcbb498b079655072ef
出典データセット
uspto-grants-1993_05
特許番号
US05210212

関連ノート

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