Hydrogen Bromide → 1-Amino-7-methyl-isoquinolin-6-ol hydrobromide

HRID 1366755Notes

Reaction equation

C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[CH3:13])[C:9]([NH2:14])=[N:8][CH:7]=[CH:6]2.[BrH:15]>>[BrH:15].[NH2:14][C:9]1[C:10]2[C:5](=[CH:4][C:3]([OH:2])=[C:12]([CH3:13])[CH:11]=2)[CH:6]=[CH:7][N:8]=1

Participants

Reactant 2

HCID 260Hydrogen Bromide

HCID 669417806-Methoxy-7-methylisoquinolin-1-ylamine

Product 1

HCID 1363789971-Amino-7-methyl-isoquinolin-6-ol hydrobromide

Conditions

Temperature: 125 °C

Procedure

A mixture of 6-methoxy-7-methylisoquinolin-1-ylamine (5.11 g, 27.18 mmol) and 48% aqueous hydrobromic acid (150 ml) was heated at 125° C. for 2 days. The mixture was concentrated in vacuo and triturated with diethyl ether, dried in vacuo to give 1-amino-7-methyl-isoquinolin-6-ol hydrobromide (5 g), EIMS: m/z=175.1 [M+H]+. 1H NMR (DMSO-D6) δ7.06 (1H, d), 7.16 (1H, d) , 7.25 (1H, dd), 7.56 (1H, d), 8.44 (1H, dd), 8.66 (2H, broad s), 11.05 (1H, s), 12.45 (1H, s).

Workup

concentrationThe mixture was concentrated in vacuo
customtriturated with diethyl ether
customdried in vacuo

Sources & evidence

ORD record: ord-7f948bbccd074059a0584d189322bc13
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07893088B2

Reaction notes

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