Chloroform → 4-Bromo-1-methoxyisoquinoline

HRID 1921328ノート

反応式

HRID 1921328 の反応式
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[NH:4][C:3]=1C.[CH:14](Cl)(Cl)Cl.IC>C(=O)([O-])[O-].[Ag+2].C(N(CC)CC)C>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH3:14])=[N:4][CH:3]=1

参加物

6

反応物 3

HCID 6212ChloroformHCID 6328Methyl iodideHCID 67492305HCID 67492305、化合物

生成物 1

HCID 247666564-Bromo-1-methoxyisoquinoline収率 60%

試薬・触媒・溶媒 2

HCID 178418647HCID 178418647、化合物触媒HCID 8471Triethylamine溶媒

実験手順

To a stirred suspension of 4-bromo-3-methyl-2H-isoquinolin-1-one (1.86 g, 7.81 mmol), silver carbonate (2.92 g, 10.6 mmol) and chloroform (150 mL) is added dropwise over 10 min iodomethane (7.3 mL, 117 mmol) and the mixture is stirred in the dark for 3 d. Triethylamine is added and the solids are removed by filtration through a pad of Celite. The filtrate is concentrated and the residue is purified by chromatography eluting with dichloromethane. Product containing fractions are combined and concentrated to afford 4-bromo-1-methoxyisoquinoline (1.19 g, 60% yield) as an oil that solidified on standing. LC/MS: MS m/e=252/254 (M+H); RT 4.68; 1H NMR (CDCl3, δ ppm) 8.19 (1H, d), 8.09 (1H, d), 7.71 (1H, t), 7.50 (1H, t), 4.10 (3H, s); 2.71 (3H, s).

後処理

  1. customthe solids are removed by filtration through a pad of Celite
  2. concentrationThe filtrate is concentrated
  3. customthe residue is purified by chromatography
  4. washeluting with dichloromethane
  5. additionProduct containing fractions
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-86b3369fd6614ea9a04def80da64e725
出典データセット
uspto-grants-2012_05
特許番号
US08173682B2

反応ノート

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