Ammonium Hydroxide → 3-(p-Chlorophenyl)-2-[2-(diethylamino)ethyl]isoindole-1-carboxylic acid ethyl ester hydrochloride

HRID 1973310ノート

反応式

HRID 1973310 の反応式
[CH2:1]([N:3]([CH2:7][CH3:8])[CH2:4][CH2:5][NH2:6])[CH3:2].[CH2:9]([O:11][C:12](=[O:30])[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21](=O)[C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=1)=O)[CH3:10].[OH-].[NH4+]>C(O)=O>[ClH:28].[CH2:9]([O:11][C:12]([C:13]1[N:6]([CH2:5][CH2:4][N:3]([CH2:7][CH3:8])[CH2:1][CH3:2])[C:21]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)=[C:16]2[C:15]=1[CH:20]=[CH:19][CH:18]=[CH:17]2)=[O:30])[CH3:10]

参加物

5

反応物 3

HCID 14923Ammonium HydroxideHCID 60993N,N-DiethylethylenediamineHCID 53699063HCID 53699063、化合物

生成物 1

HCID 706202883-(p-Chlorophenyl)-2-[2-(diethylamino)ethyl]isoindole-1-carboxylic acid ethyl ester hydrochloride

試薬・触媒・溶媒 1

HCID 284Formic Acid溶媒

実験手順

A mixture of 0.83 g. of formic acid and 1.05 g. of 2-diethylaminoethylamine is treated at room temperature with 0.95 g. of [o-(p-chlorobenzoyl)phenyl]glyoxylic acid ethyl ester and subsequently stirred at 140° C. for 2 hours. After cooling, the obtained solution is made alkaline with 2-N ammonium hydroxide with addition of ice and extracted with ether. The extract, shielded from daylight, is washed with water, dried over sodium sulfate, concentrated and chromatographed on 70 g. of silica gel with ether as the eluant. The homogeneous fractions are combined, concentrated to a volume of 15-20 ml. and treated with ethereal hydrochloric acid. The crystallized hydrochloride is removed by filtration and washed with ether, and there is obtained 3-(p-chlorophenyl)-2-[2-(diethylamino)ethyl]isoindole-1-carboxylic acid ethyl ester hydrochloride; melting point 202°-204° C. (decomposition). Recrystallization from methylene chloride/ether does not increase the melting point.

後処理

  1. additionA mixture of 0.83 g
  2. temperatureAfter cooling
  3. additionwith addition of ice
  4. extractionextracted with ether
  5. washis washed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customchromatographed on 70 g
  9. concentrationconcentrated to a volume of 15-20 ml
  10. additionand treated with ethereal hydrochloric acid
  11. customThe crystallized hydrochloride is removed by filtration
  12. washwashed with ether

出典と根拠

ORDレコード
ord-d479646bdab447c1bd60acae5e438cff
出典データセット
uspto-grants-1976_12
特許番号
US03996374

反応ノート

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