Water → 1-Amino-4-bromo-6-fluoro-isoquinoline

HRID 2244067Notes

Reaction equation

HRID 2244067 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:12])=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.C1C(=O)N([Br:20])C(=O)C1.O>C(Cl)(Cl)Cl>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:12])=[CH:9][CH:10]=2)[C:5]([Br:20])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 250594376-Fluoroisoquinolin-1-amine

Product 1

HCID 250594381-Amino-4-bromo-6-fluoro-isoquinolineYield 65%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 1-amino-6-fluoro-isoquinoline (0.41 g, 2.53 mmol) in CHCl3 (25 mL) is added NBS (0.45 g, 2.53 mmol), and the reaction mixture is stirred RT for 1.5 h. The reaction mixture is treated with water (10 mL). The aqueous phase is extracted with CH2Cl2 (2×). The combined organic layers are washed with brine, and dried over MgSO4. The solvent is evaporated and the residue is dried under vacuum. Purification of the crude material using a Biotage column (10-40% MeOH/CH2Cl2) afforded 0.395 g (65%) of 1-amino-4-bromo-6-fluoro-isoquinoline. LC/MS m/z=242 [M+H]+.

Workup

  1. extractionThe aqueous phase is extracted with CH2Cl2 (2×)
  2. washThe combined organic layers are washed with brine
  3. dry with materialdried over MgSO4
  4. customThe solvent is evaporated
  5. customthe residue is dried under vacuum
  6. customPurification of the crude material

Sources & evidence

ORD record
ord-3fc3988f8edd4947aa7422e84c3e3061
Source dataset
uspto-grants-2010_03
Patent number
US07678803B2

Reaction notes

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