Methanol → 2-[5-Chloro-2-hydroxy benzyl]isoindole-1,3-dione

HRID 11638

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.ClC[C:11]1[CH:19]=[CH:18][CH:17]=[C:13]([C:14](N)=[O:15])[C:12]=1[C:20]([NH2:22])=[O:21].[CH3:23]O>[Cl-].[Zn+2].[Cl-]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH:3]=1)[CH2:23][N:22]1[C:20](=[O:21])[C:12]2[C:13](=[CH:17][CH:18]=[CH:19][CH:11]=2)[C:14]1=[O:15]

Participants

Conditions

Temperature: 90 °C

Procedure

To 4-chlorophenol (2.0 g, 15.5 mmol) and chloromethylphthalamide (2.62 g, 13.4 mmol) was added zinc chloride (3 mL, 0.5 M in tetrahydrofuran, 1.5 mmol). The reaction was stirred at 90° C. for 48 hours. After cooling the reaction was diluted with methanol (15 mL) and brought to reflux. After 30 minutes the hot suspension was filtered through a medium glass frit and concentrated to an off-white solid. Methanol (50 mL) was again added and the reaction brought to reflux. After 3 hours the hot suspension was filtered through a medium glass frit and concentrated to an off-white solid. The crude product was purified via chromatography on silica gel to give the title compound (3.86 g).

Workup

temperatureAfter cooling the reaction
temperatureto reflux
filtrationAfter 30 minutes the hot suspension was filtered through a medium glass frit
concentrationconcentrated to an off-white solid
additionMethanol (50 mL) was again added
temperatureto reflux
filtrationAfter 3 hours the hot suspension was filtered through a medium glass frit
concentrationconcentrated to an off-white solid
customThe crude product was purified via chromatography on silica gel

Sources & evidence

ORD record: ord-e670c84d8b25493984d67a7d7e5b877b
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07098212B2

Linked notes

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