Ammonia → 5-Bromo-1-chloro-6-hydroxyisoquinoline

HRID 1436013Notes

Reaction equation

HRID 1436013 reaction equation
B(Br)(Br)Br.[Br:5][C:6]1[C:15]([O:16]C)=[CH:14][CH:13]=[C:12]2[C:7]=1[CH:8]=[CH:9][N:10]=[C:11]2[Cl:18].N>ClCCl>[Br:5][C:6]1[C:15]([OH:16])=[CH:14][CH:13]=[C:12]2[C:7]=1[CH:8]=[CH:9][N:10]=[C:11]2[Cl:18]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 25134Boron tribromideHCID 579564605-Bromo-1-chloro-6-methoxyisoquinoline

Product 1

HCID 1363374885-Bromo-1-chloro-6-hydroxyisoquinolineYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1M BBr3 in dichloromethane (25.5 ml) was added dropwise to a stirred solution of 5-bromo-1-chloro-6-methoxyisoquinoline (1.26 g) in dichloromethane at 10° C. The mixture was stirred at ambient temperature for 48 h then poured into ice-water and the pH adjusted to 8 by adding concentrated aqueous ammonia. The mixture was extracted with ethyl acetate (x 2) and the aqueous phase then acidified to pH ˜4 using dilute hydrochloric acid. The aqueous phase was extracted with ethyl acetate (x 2), the combined organics were dried (Na2SO4) and concentrated in vacuo to give 5-bromo-1-chloro-6-hydroxyisoquinoline (1.1 g), El-MS: m/z=257.9, 260.0 and 261.6 [M+H]+.

Workup

  1. extractionThe mixture was extracted with ethyl acetate (x 2)
  2. extractionThe aqueous phase was extracted with ethyl acetate (x 2)
  3. dry with materialthe combined organics were dried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6c03ef9d9a9946419e7d45617ac64bad
Source dataset
uspto-grants-2009_11
Patent number
US07618985B2

Reaction notes

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