Ammonia → 1-Aminoisoquinolin-6-ol

HRID 1366739Notes

Reaction equation

HRID 1366739 reaction equation
B(Br)(Br)Br.[NH2:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:16]C)=[CH:13][CH:14]=2)[CH:9]=[CH:8][N:7]=1.N>ClCCl>[NH2:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([OH:16])=[CH:13][CH:14]=2)[CH:9]=[CH:8][N:7]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 25134Boron tribromideHCID 155384096-Methoxyisoquinolin-1-amine

Product 1

HCID 1357539911-Aminoisoquinolin-6-olYield 88.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of boron tribromide (18.2 ml, 370 mmol) in 20 ml dichloromethane was added dropwise to a stirred solution of 1-amino-6-methoxyisoquinoline (11.0 g, 63 mmol) in 150 ml of dichloromethane at 10° C. After stirring for 4 days at ambient temperature the reaction mixture was poured into ice and the pH was adjusted to 9 by adding concentrated aqueous ammonia. The precipitated material was collected by filtration and dried in vacuo to give 1-amino-6-hydroxyisoquinoline (8.9 g, 88%), EI-MS: 160 [M]+

Workup

  1. additionwas poured into ice
  2. filtrationThe precipitated material was collected by filtration
  3. customdried in vacuo

Sources & evidence

ORD record
ord-5f59f222d4c446bab0907590bc9d860d
Source dataset
uspto-grants-2011_02
Patent number
US07893088B2

Reaction notes

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