Sulfuric Acid → Methyl 5-bromoisoquinoline-4-carboxylate

HRID 1470482Notes

Reaction equation

HRID 1470482 reaction equation
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

Participants

4

Reactant 3

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

Product 1

HCID 68281832Methyl 5-bromoisoquinoline-4-carboxylateYield 90.2%

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-9f895bbcf45840f2a5ec6561f168bb49
Source dataset
uspto-grants-2015_04
Patent number
US09006442B2

Reaction notes

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