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

HRID 1390841

反応式

HRID 1390841 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-l. 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 12N 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-9N 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-9N 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-1371b11e56b84597954a8862872a05ea
出典データセット
uspto-grants-1979_02
特許番号
US04140697

関連ノート

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