Benzaldehyde → Benzyl(4-bromoisoquinolin-8-yl)amine

HRID 1454937Notes

Reaction equation

HRID 1454937 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:19]=1[CH:18]=[N:17][CH:16]=[C:15]2[Br:20].C([BH3-])#N.[Na+]>CCO.CCOC(C)=O>[CH2:1]([NH:9][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:19]=1[CH:18]=[N:17][CH:16]=[C:15]2[Br:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 4597724-Bromoisoquinolin-8-amine2×HCID 5003444Sodium cyanoborohydride

Product 1

HCID 22352481Benzyl(4-bromoisoquinolin-8-yl)amine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

Under argon, benzaldehyde (584 μl, 5.75 mmol) is added to a solution of 8-amino-4-bromoisoquinoline (Intermediate 23.2, 1.11 g, 5 mmol) in absolute EtOH (60 ml). The mixture is heated at 90° C. for 24 h. It is cooled to 0° C. and then sodium cyanoborohydride (NaBH3CN, 3.3 g, 50 mmol) is added in small portions. The stirring is maintained for 2 h at room temperature. The reaction mixture is diluted with AcOEt (600 ml) and is then washed with water. The organic phase is dried over Na2SO4 and then evaporated. The residue is purified on silica gel, eluting with an AcOEt/petroleum ether (1/4) mixture.

Workup

  1. temperatureIt is cooled to 0° C.
  2. temperatureThe stirring is maintained for 2 h at room temperature
  3. washis then washed with water
  4. dry with materialThe organic phase is dried over Na2SO4
  5. customevaporated
  6. customThe residue is purified on silica gel
  7. washeluting with an AcOEt/petroleum ether (1/4) mixture

Sources & evidence

ORD record
ord-0d1955cf007f4177b6b6d6bcb1473c9d
Source dataset
uspto-grants-2009_01
Patent number
US07482342B2

Reaction notes

Loading…