Hydrochloric Acid → Alpha-amino-6-chloro-3-indoleacrylic acid methylester hydrochloride

HRID 127499

反応式

HRID 127499 の反応式
Cl.CO.[CH3:4][O:5][C:6](=[O:22])[C:7]([N+:19]([O-])=O)=[CH:8][C:9]1[C:17]2[C:12](=[CH:13][C:14]([Cl:18])=[CH:15][CH:16]=2)[NH:11][CH:10]=1>CCOCC>[ClH:18].[CH3:4][O:5][C:6](=[O:22])[C:7]([NH2:19])=[CH:8][C:9]1[C:17]2[C:12](=[CH:13][C:14]([Cl:18])=[CH:15][CH:16]=2)[NH:11][CH:10]=1

参加物

5

反応物 3

HCID 313Hydrochloric Acid2 回HCID 887MethanolHCID 53746644Alphanitro-6-chloro-3-indoleacrylic acid methylester

生成物 1

HCID 70550909Alpha-amino-6-chloro-3-indoleacrylic acid methylester hydrochloride収率 180.1%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

A 3-1. three-necked flask, equipped with a thermometer and a mechanical stirrer was charged with 316 g (1.4 moles) of stannous chloride dihydrate and a solution of 111 g (3 moles) of dry hydrogen chloride gas in 1 l. of methyl alcohol. The colorless solution was stirred and cooled to -30° in a dry ice-acetone bath. 112.3 g (0.40 moles) of alpha-nitro-6-chloro-3-indoleacrylic acid methylester was added in 4 equal portions over 1 hour, maintaining the temperature between -25° and -20°. After the addition was complete, the temperature was allowed to rise to -10° and stirring at this temperature was continued for 90 minutes. Then 500 ml. of ether was added to the yellow suspension, followed by addition of 500 ml of 12 N hydrochloric acid (concentrated), the temperature was kept below 5°. The mixture was then filtered through a Buchner funnel. The filter cake was washed with 1000 ml of methyl alcohol-9 N aqueous hydrochloric acid 1:1, precooled to -20°, and 400 ml of ether. The tan product was dried at 40°/0.1 mmHg for 8 hours and then at 20°/0.1 mmHg to constant weight to yield 103.4 g (90%) of crude product, m.p. 191° (dec.).

後処理

  1. customthree-necked flask, equipped with a thermometer and a mechanical stirrer
  2. temperaturecooled to -30° in a dry ice-acetone bath
  3. temperaturemaintaining the temperature between -25° and -20°
  4. additionAfter the addition
  5. customto rise to -10°
  6. stirringstirring at this temperature
  7. customwas kept below 5°
  8. filtrationThe mixture was then filtered through a Buchner funnel
  9. washThe filter cake was washed with 1000 ml of methyl alcohol-9 N aqueous hydrochloric acid 1:1
  10. customprecooled to -20°
  11. customThe tan product was dried at 40°/0.1 mmHg for 8 hours

出典と根拠

ORDレコード
ord-a0e4707512d94dd9990a5c981d0f41ff
出典データセット
uspto-grants-1981_03
特許番号
US04256641

関連ノート

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