Water → HCID 22175431, compound

HRID 1797478Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH3:13])[C:6]([CH2:14][N:15]1[C:23](=[O:24])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]1=[O:25])=[C:5]2[C:26]1[CH:31]=[CH:30][C:29]([O:32]C)=[CH:28][CH:27]=1.B(Br)(Br)Br.O>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH3:13])[C:6]([CH2:14][N:15]1[C:16](=[O:25])[C:17]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:23]1=[O:24])=[C:5]2[C:26]1[CH:27]=[CH:28][C:29]([OH:32])=[CH:30][CH:31]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2-{[6-chloro-4-(4-methoxyphenyl)-2-methyl-1-oxo-1,2-dihydro-3-isoquinolinyl]methyl}-1H-isoindole-1,3(2H)-dione (synthesized according to the method similar to that in Example 16(7)) (0.92 g, 2 mmol) in dichloromethane (10 ml) was added boron tribromide, (76 ml, 36 mmol) at 0° C. and the mixture was stirred at 0° C. for 1 h. The reaction mixture was poured into water and extracted with ethyl acetate. After washing the extract with water, the extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized from tetrahydrofuran-diisopropyl ether to give 2-{[6chloro-4-(4-hydroxyphenyl)-2-methyl-1-oxo-1,2-dihydro-3-isoquinolinyl]methyl}-1H-isoindole-1,3(2H)-dione (0.83 g, 94.3%) as crystals.

Workup

extractionextracted with ethyl acetate
washAfter washing the
extractionextract with water
dry with materialthe extract was dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was recrystallized from tetrahydrofuran-diisopropyl ether

Sources & evidence

ORD record: ord-e9aab15160e54e33a15ec09f93969031
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07034039B2

Reaction notes

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