Potassium Carbonate → HCID 18992051, compound

HRID 375764Notes

Reaction equation

[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[C:12]1[CH:13]=[C:14]([OH:22])[C:15]([CH3:21])=[C:16]([CH:20]=1)[C:17]([OH:19])=[O:18].[N+:23]([C:26]1[CH:33]=[CH:32][C:29]([CH2:30]Br)=[CH:28][CH:27]=1)([O-:25])=[O:24].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[C:12]1[CH:13]=[C:14]([OH:22])[C:15]([CH3:21])=[C:16]([CH:20]=1)[C:17]([O:19][CH2:30][C:29]1[CH:32]=[CH:33][C:26]([N+:23]([O-:25])=[O:24])=[CH:27][CH:28]=1)=[O:18]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 120 mg of 5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-2-methylbenzoic acid, 87 mg of 4-nitrobenzyl bromide and 139 mg of potassium carbonate in 3 ml of dimethylformamide was stirred at 0° C. for 4 hours. The solvent was evaporated in vacuo, and the residue was triturated with a mixture of methylene chloride and saturated sodium bicarbonate solution. The unsoluble material was isolated by filtration to yield 190 mg of p-nitrobenzyl 5-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-3-hydroxy-2-methylbenzoate, m.p. 210°-244° C.

Workup

customThe solvent was evaporated in vacuo
customthe residue was triturated with a mixture of methylene chloride and saturated sodium bicarbonate solution
customThe unsoluble material was isolated by filtration

Sources & evidence

ORD record: ord-221ff42c66e24c25861037de2c69fb1e
Source dataset: uspto-grants-1996_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05486466

Reaction notes

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