N-(2,2-diethoxyethyl)-3-methoxy-2-nitrobenzamide → 7-methoxy-8-nitroisoquinolin-1(2H)-one

HRID 577487Notes

Reaction equation

C(O[CH:4](OCC)[CH2:5][NH:6][C:7](=[O:19])[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[C:9]=1[N+:16]([O-:18])=[O:17])C>S(=O)(=O)(O)O>[CH3:15][O:14][C:10]1[C:9]([N+:16]([O-:18])=[O:17])=[C:8]2[C:13]([CH:4]=[CH:5][NH:6][C:7]2=[O:19])=[CH:12][CH:11]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of N-(2,2-diethoxyethyl)-3-methoxy-2-nitrobenzamide (296a, 92 g, 0.295 mol) in concentrated sulfuric acid (1 L) was stirred at 70° C. for three hours. After cooling to room temperature, the mixture was slowly poured into ice water (3 L), causing a solid precipitate to form. The precipitate was collected by filtration. The filter cake was washed with water (1 L) and dried to yield 7-methoxy-8-nitroisoquinolin-1(2H)-one (296b, 60 g, 92% yield) as a brown solid. 1H NMR (400 MHz, DMSO-d6) δ 7.92-7.89 (d, J=9.2 Hz, 1H), 7.81-7.79 (d, J=9.2 Hz, 1H), 7.18-7.15 (t, J=6.6 Hz, 1H), 6.66-6.64 (d, J=7.2 Hz, 1H), 3.95 (s, 3H).

Workup

temperatureAfter cooling to room temperature
customto form
filtrationThe precipitate was collected by filtration
washThe filter cake was washed with water (1 L)
customdried

Sources & evidence

ORD record: ord-92f63782e292472aa0bb5b440c2aa432
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040515B2

Reaction notes

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