Hydrochloric Acid → 4-methyl-3-[7-(4-methylpiperazin-1-yl)-1-oxoisoquinolin-2(1H)-yl]benzoic acid

HRID 506983Notes

Reaction equation

[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[CH:4][C:3]=1[N:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][C:16]([N:22]3[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]3)=[CH:17][CH:18]=2)[C:13]1=[O:29].[OH-].[Na+].Cl>CO>[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][C:16]([N:22]3[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]3)=[CH:17][CH:18]=2)[C:13]1=[O:29]

Participants

Conditions

Temperature: 65 °C

Procedure

To a stirred solution of methyl 4-methyl-3-[7-(4-methylpiperazin-1-yl)-1-oxoisoquinolin-2(1H)-yl]benzoate (272 mg) in methanol was added 1N NaOH solution (0.85 ml) and the reaction mixture was stirred at 65° C. for 30 minutes and then neutralized with 1N HCl. After cooling to room temperature the resulting precipitate was collected by filtration and washed with water, ethyl acetate, methanol and then air-dried to yield 4-methyl-3-[7-(4-methylpiperazin-1-yl)-1-oxoisoquinolin-2(1H)-yl]benzoic acid (166 mg) as a pale yellow solid; NMR Spectrum: (DMSOd6) 2.12 (s, 3H), 2.25 (s, 3H), 2.50 (m, 4H), 3.27 (m, 4H), 6.64 (d, 1H), 7.12 (d, 1H), 7.56 (m, 2H), 7.60 (s, 1H), 7.63 (d, 1H), 7.75 (s, 1H), 7.94 (d, 1H); Mass Spectrum: M+H+ 378.

Workup

temperatureAfter cooling to room temperature the resulting precipitate
filtrationwas collected by filtration
washwashed with water, ethyl acetate, methanol
customair-dried

Sources & evidence

ORD record: ord-bc7f7a998ad14edb9e3835364b94c34d
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07786115B2

Reaction notes

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