Methanol → methyl 3-(7-hydroxy-1-oxoisoquinolin-2(1H)-yl)-4-methylbenzoate

HRID 506980Notes

Reaction equation

[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]([C:13]3[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=3[CH3:22])[C:16]([OH:18])=[O:17])[C:9]2=[O:12])=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH3:27]N(C=O)C.CO>C(Cl)Cl>[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]([C:13]3[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=3[CH3:22])[C:16]([O:18][CH3:27])=[O:17])[C:9]2=[O:12])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a stirred solution of 3-(7-hydroxy-1-oxoisoquinolin-2(1H)-yl)-4-methylbenzoic acid (440 mg) and thionyl chloride (0.131 ml) in methylene chloride (8 ml) was added DMF (0.14 ml) and the solution was heated at 40° C. for 2 hours. The reaction mixture was allowed to cool to room temperature before the addition of methanol (5 ml) and stirring continued for 2.5 hours. The reaction mixture was concentrated and then dissolved in ethyl acetate and washed with saturated aqueous sodium hydrogen carbonate (2×), brine, dried (magnesium sulfate) and concentrated to yield the crude methyl 3-(7-hydroxy-1-oxoisoquinolin-2(1H)-yl)-4-methylbenzoate as a brown solid (419 mg); NMR Spectrum: (DMSOd6) 2.14 (s, 3H), 3.87 (s, 3H), 6.65 (d, 1H), 7.11 (d, 1H), 7.23 (d, 1H), 7.57-7.62 (m, 3H), 7.80 (s, 1H), 7.97 (d, 1H), 10.00 (s, 1H); Mass Spectrum: M+Na+ 332.

Workup

concentrationThe reaction mixture was concentrated
dissolutiondissolved in ethyl acetate
washwashed with saturated aqueous sodium hydrogen carbonate (2×), brine
dry with materialdried (magnesium sulfate)
concentrationconcentrated

Sources & evidence

ORD record: ord-f4074ee2f8a040bbb13a729b4ed545ca
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07786115B2

Reaction notes

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