Ammonia → 5-Bromo-4-methylisoquinoline

HRID 10555Notes

Reaction equation

HRID 10555 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[N:4][CH:3]=1.[Br:12]N1C(=O)CCC1=O.N>S(=O)(=O)(O)O>[Br:12][C:10]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:11]=1[C:2]([CH3:1])=[CH:3][N:4]=[CH:5]2

Participants

5

Reactant 3

HCID 222AmmoniaHCID 67184N-bromobutanimideHCID 640939Isoquinoline, 4-methyl-

Product 1

HCID 219798825-Bromo-4-methylisoquinoline

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

4-Methylisoquinoline (0.1 ml, synthesized according to the method described in Tetrahedron. Lett. 34, 45, 7239 (1993)) was dissolved in concentrated sulfuric acid (1 ml), then added with N-bromosuccinimide (125 mg) with ice cooling and stirred for 2 hours. The reaction mixture was added with 28% aqueous ammonia (5 ml) and extracted twice with dichloromethane (10 ml for each time). The organic layer was dried over anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=50:1) to obtain the title compound (108 mg).

Workup

  1. extractionextracted twice with dichloromethane (10 ml for each time)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (chloroform:methanol=50:1)

Sources & evidence

ORD record
ord-4b5eef1a0b364453826833678fecada6
Source dataset
uspto-grants-2006_08
Patent number
US07094789B2

Reaction notes

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