Sulfuric Acid → 5-Bromoisoquinoline-8-sulfonic acid

Reaction equation

[S:1](=[O:5])(=O)([OH:3])[OH:2].[Br:6][C:7]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:8]=1[CH:9]=[CH:10][N:11]=[CH:12]2>>[Br:6][C:7]1[CH:16]=[CH:15][C:14]([S:1]([OH:3])(=[O:5])=[O:2])=[C:13]2[C:8]=1[CH:9]=[CH:10][N:11]=[CH:12]2

Participants

Reactant 2

HCID 1118Sulfuric Acid

HCID 7364875-Bromoisoquinoline

Product 1

HCID 534150725-Bromoisoquinoline-8-sulfonic acidYield 90%

Procedure

To fuming sulfuric acid at 0° C. was added 5-bromoisoquinoline (20.0 g, 96 mmol), The resultant mixture was warmed to 200° C. for 4 h and was then cooled to rt and poured into 500 mL of ice water. The product was removed via filtration, washed with water and acetone, and dried to give 25 g (90%) of a white solid.

Workup

customat 0° C.
customThe product was removed via filtration
washwashed with water and acetone
customdried

Sources & evidence

ORD record: ord-cf88438e16db476d8a3ae552819f297f
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07268142B2

Reaction notes

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