Ethyl Acetate → 3-(7-hydroxy-1-oxo-1H-isoquinolin-2-yl)-4-methylbenzoic acid

HRID 506972Notes

Reaction equation

C1(N[C:5](=[O:25])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([N:13]3[CH:22]=[CH:21][C:20]4[C:15](=[CH:16][C:17]([OH:23])=[CH:18][CH:19]=4)[C:14]3=[O:24])[CH:7]=2)CC1.C(OCC)(=[O:28])C>Br>[OH:23][C:17]1[CH:16]=[C:15]2[C:20]([CH:21]=[CH:22][N:13]([C:8]3[CH:7]=[C:6]([CH:11]=[CH:10][C:9]=3[CH3:12])[C:5]([OH:28])=[O:25])[C:14]2=[O:24])=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 150 °C

Procedure

N-Cyclopropyl-3-(7-hydroxy-1-oxoisoquinolin-2(1H)-yl)-4-methylbenzamide (0.5 g) was stirred in 48% hydrobromic acid (7 mL) and heated under microwave irradiation conditions (Personal Chemistry Emrys Optimizer with 300 W magnetron) at 150° C. for 1 hour. The reaction mixture was diluted with ethyl acetate, washed water (×3), brine, dried (magnesium sulfate) and concentrated to a brown solid. The solid was triturated with diethyl ether to yield 3-(7-hydroxy-1-oxoisoquinolin-2(1H)-yl)-4-methylbenzoic acid as a brown solid (0.32 g); NMR Spectrum: (DMSOd6) 2.11 (s, 3H), 6.65 (d, 1H), 7.12 (d, 1H), 7.27 (d, 1H), 7.54 (d, 1H), 7.60 (s, 1H), 7.61 (d, 1H), 7.78 (s, 1H), 7.95 (d, 1H), 10.09 (s, 1H), 13.05 (s, 1H); Mass Spectrum: M+H+ 296.

Workup

washwashed water (×3), brine
dry with materialdried (magnesium sulfate)
concentrationconcentrated to a brown solid
customThe solid was triturated with diethyl ether

Sources & evidence

ORD record: ord-3e1c7ec359f34a359da219a9bb545f20
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07786115B2

Reaction notes

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