Ammonia → 1-Aminoisoquinolin-6-ol

HRID 1070557Notes

Reaction equation

HRID 1070557 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 of dichloromethane was added dropwise to a stirred solution of 1-amino-6methoxy-isoquinoline (1d, 11.0 g; 63 mmol) in 150 mL of dichloromethane at 10° C. After stirring for 4 d 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 8.9 g (88%) of the title compound as a white solid; m.p. 258-260° C.; El-MS: 160 (M+). 1H NMR (DMSO-d6): δ 8.11 (d, 1H), 7.65 (d, 1H), 6.99 (dd, 1H), 6.86 (d, 1H), 6.80-6.63 (m, 4H), 5.2 (bs, 1H).

Workup

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

Sources & evidence

ORD record
ord-50a60e14f11a4aadbb911410387509dd
Source dataset
uspto-grants-2005_06
Patent number
US06903107B1

Reaction notes

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