Sulfuric Acid → Methyl 5-bromoisoquinoline-4-carboxylate

HRID 1470482ノート

反応式

HRID 1470482 の反応式
OS(O)(=O)=O.[CH:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:16]([O:18][CH3:19])=[O:17])=[CH:8][N:7]=1.C1C(=O)N([Br:27])C(=O)C1>>[Br:27][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:10]=1[C:9]([C:16]([O:18][CH3:19])=[O:17])=[CH:8][N:7]=[CH:6]2

参加物

4

反応物 3

HCID 1118Sulfuric AcidHCID 67184N-bromobutanimideHCID 11830161Methyl Isoquinoline-4-carboxylate

生成物 1

HCID 68281832Methyl 5-bromoisoquinoline-4-carboxylate収率 90.2%

実験手順

To a mixture of conc. H2SO4 (16 mL) and methyl isoquinoline-4-carboxylate (Intermediate-15) (2.8 g, 15 mmol) at 0° C. was added, NBS (3.3 g, 18.7 mmol) slowly and the reaction mixture was allowed to come to RT and stirred overnight. After completion (TLC), it was quenched with ice, neutralized (NaHCO3) and extracted with EtOAc (50 mL×3). The organic phase was separated, dried (Na2SO4) and concentrated to give dark brown oil (3.6 g) as crude product that was purified by flash column chromatography (25% EtOAc in Hexanes) to furnish the desired compound (1.4 g, 35%).

後処理

  1. additionwas added
  2. customto come to RT
  3. customAfter completion (TLC), it was quenched with ice
  4. extractionextracted with EtOAc (50 mL×3)
  5. customThe organic phase was separated
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-9f895bbcf45840f2a5ec6561f168bb49
出典データセット
uspto-grants-2015_04
特許番号
US09006442B2

反応ノート

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