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4-Chlorobenzylamine → N-(4-Chlorobenzyl)-2-(hydroxymethyl)-8-iodo-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxamide

HRID 1168503
ノート
印刷プレビュー

反応式

HRID 1168503 の反応式
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1.C([O:13][CH2:14][CH:15]1[N:25]2[C:26]3[C:21]([C:22](=[O:32])[C:23]([C:27](OCC)=[O:28])=[CH:24]2)=[CH:20][C:19]([I:33])=[CH:18][C:17]=3[CH2:16]1)(=O)C>C(Cl)Cl.CCOC(C)=O.CO>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:7][C:27]([C:23]2[C:22](=[O:32])[C:21]3[C:26]4=[C:17]([CH2:16][CH:15]([CH2:14][OH:13])[N:25]4[CH:24]=2)[CH:18]=[C:19]([I:33])[CH:20]=3)=[O:28])=[CH:4][CH:3]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 660364-ChlorobenzylamineHCID 12083027Ethyl 2-((Acetyloxy)methyl)-8-iodo-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]-quinoline-5-carboxylate

生成物 1

HCID 12083028N-(4-Chlorobenzyl)-2-(hydroxymethyl)-8-iodo-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxamide収率 43%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 6344Dichloromethane
溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

A mixture of 4-chlorobenzylamine (2 mL) and ethyl 2-((acetyloxy)methyl)-8-iodo-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxylate (Preparation 9, 0.70 g) is heated to 120° C. under a stream of nitrogen for 7 h, to 100° C. for 18 h, and then to 130° C. for 8 hours. Upon cooling, the mixture is diluted with a mixture of CH2Cl2, EtOAc, and methanol (2/2/1) and absorbed onto silica gel. This material is chromatographed eluting with 0-4% methanol in CH2Cl2 to give a wet brown solid. The crude product is recrystallized by dissolving in hot acetic acid and slowly adding water until cloudiness persisted. Upon standing, crystals form which are collected to provide 340 mg (43%) of the title compound as a tan solid. Physical characteristics: M.p. 222-223° C.; MS (ESI+) m/z 495 (M+H)+.

後処理

  1. temperatureUpon cooling
  2. customabsorbed onto silica gel
  3. customThis material is chromatographed
  4. washeluting with 0-4% methanol in CH2Cl2
  5. customto give a wet brown solid
  6. customThe crude product is recrystallized
  7. dissolutionby dissolving in hot acetic acid
  8. customcrystals form which are collected

出典と根拠

ORDレコード
ord-8626b552b82d49aeb0f1c14cc2bc560c
出典データセット
uspto-grants-2003_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06624159B2

反応ノート

読み込み中…

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