Hydrochloric Acid → 1-Aminoisoquinoline-6-carboxylic acid hydrochloride

HRID 1279025Notes

Reaction equation

C([NH:9][C:10]1[C:19]2[C:14](=[CH:15][C:16]([C:20]([OH:22])=[O:21])=[CH:17][CH:18]=2)[CH:13]=[CH:12][N:11]=1)(=O)C1C=CC=CC=1.[ClH:23]>C(O)(=O)C>[ClH:23].[NH2:9][C:10]1[C:19]2[C:14](=[CH:15][C:16]([C:20]([OH:22])=[O:21])=[CH:17][CH:18]=2)[CH:13]=[CH:12][N:11]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 445 mg [1-(benzoylamino)-6-isoquinolinyl]carboxylic acid, 10 mL of acetic acid and 20 mL of 4N hydrochloric acid was heated at 100° C. for one day. The reaction mixture was concentrated and coevaporated with 0.5N hydrochloric acid. The resulting residue was triturated with diethyl ether to yield 341 mg of the title compound. 1H-NMR 200 MHz (CD3OD) δ: 7.35 (1H, dd, J=1 Hz and J=7 Hz), 7.63 (1H, d, J=7 Hz), 8.30 (1H, dd, J=2 Hz and J=8 Hz), 8.49-8.57 (2H, m).

Workup

concentrationThe reaction mixture was concentrated
customThe resulting residue was triturated with diethyl ether

Sources & evidence

ORD record: ord-bbd369adc0d141339d2ffd0e90d1a15a
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06444672B1

Reaction notes

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