Water → 2,3-dihydro-6-methoxy-2-(3-pyridylmethyl)-1H-isoindole-1-one

HRID 1609597Notes

Reaction equation

[H-].[Na+].C(O[CH2:7][C:8]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][C:9]=1[C:10]([NH:12][CH2:13][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1)=[O:11])(=O)C.O.C1(C)C=CC=CC=1>CN(C)C=O>[CH3:25][O:24][C:21]1[CH:20]=[C:9]2[C:8]([CH2:7][N:12]([CH2:13][C:14]3[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=3)[C:10]2=[O:11])=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of 136 mg of sodium hydride (about 60%) in 7 ml of dimethylformamide chilled at 0° C. was added 820 mg of 2-acetoxymethyl-5-methoxy-N-(3-pyridylmethyl) benzamide and the resultant mixture was stirred at room temperature for 2 hours. The reaction mixture was mixed with water and shaken with toluene. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated in vacuo. The resultant residue was chromatographed on a column of silica gel, eluting with ethyl acetate to give 386 mg of the titled compound.

Workup

washThe organic layer was washed with water
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated in vacuo
customThe resultant residue was chromatographed on a column of silica gel
washeluting with ethyl acetate

Sources & evidence

ORD record: ord-ba36a531530d4f389bd800a5fdd62bce
Source dataset: uspto-grants-1995_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05401756

Reaction notes

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