N-bromobutanimide → 7-Benzyl-1-bromo-4-hydroxy-isoquinoline-3-carboxylic acid methyl ester

HRID 409245ノート

反応式

HRID 409245 の反応式
[CH3:1][O:2][C:3]([C:5]1[N:6]=[CH:7][C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:9]=2)=[O:4].[Br:23]N1C(=O)CCC1=O>CC#N>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([Br:23])[C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:9]=2)=[O:4]

参加物

4

反応物 2

HCID 67184N-bromobutanimideHCID 671101307-Benzyl-4-hydroxy-isoquinoline-3-carboxylic acid methyl ester

生成物 1

HCID 866170717-Benzyl-1-bromo-4-hydroxy-isoquinoline-3-carboxylic acid methyl ester収率 12.9%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A mixture of 7-benzyl-4-hydroxy-isoquinoline-3-carboxylic acid methyl ester (1 mmol, 293 mg), N-bromosuccinimide (1.2 mmol, 214 mg) and anhydrous MeCN (10 mL) was stirred at ambient temperature for 4 days before silica gel was added and the mixture was concentrated in vacuo. The residue was added on top of a chromatography column filled with silica gel. Elution with hexanes:ethyl acetate=75:25 gave the title compound as an off-white solid (48 mg); MS-(+)-ion: M+1, 79Br/81Br=372.4 and 374.4.

後処理

  1. additionwas added
  2. concentrationthe mixture was concentrated in vacuo
  3. additionThe residue was added on top of a chromatography column
  4. additionfilled with silica gel
  5. washElution with hexanes

出典と根拠

ORDレコード
ord-f1705bafeb224938a8f79017f0ab7e5b
出典データセット
uspto-grants-2014_06
特許番号
US08759373B2

反応ノート

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