5-Bromo-8-nitroisoquinoline → 5-bromo-8-nitro-1,2,3,4-tetrahydroisoquinoline

HRID 48212

Reaction equation

HRID 48212 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2.C([BH3-])#N.[Na+]>C(O)(=O)C.O>[Br:1][C:2]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[C:8]2[C:3]=1[CH2:4][CH2:5][NH:6][CH2:7]2

Participants

5

Reactant 2

HCID 8169835-Bromo-8-nitroisoquinolineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 100380655-bromo-8-nitro-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Alternatively, a solution of 5-bromo-8-nitroisoquinoline (1.0 g) in glacial acetic acid (30 mL) was cooled to 0° C. and, before freezing, was treated with sodium cyanoborohydride (1.10 g). The reaction mixture was warmed slowly to room temperature under nitrogen. The reaction mixture was diluted with water and basified. Organic layer extracts were chromatographed on silica gel as before.

Workup

  1. customOrganic layer extracts were chromatographed on silica gel as before

Sources & evidence

ORD record
ord-92c435d16a5e4d599305b982937720f7
Source dataset
uspto-grants-2004_03
Patent number
US06703391B2

Linked notes

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