1,4-Benzenedimethanol → 3-(4-Chlorophenyl)-3-(4-hydroxymethylbenzyloxy)-2-(4-nitrobenzyl)-2,3-dihydroisoindol-1-one

HRID 2199299Notes

Reaction equation

HRID 2199299 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:28])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[N:9]2[CH2:18][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=2)=[CH:4][CH:3]=1.[C:29]1([CH2:37]O)[CH:34]=[CH:33][C:32]([CH2:35][OH:36])=[CH:31][CH:30]=1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([O:28][CH2:37][C:29]3[CH:34]=[CH:33][C:32]([CH2:35][OH:36])=[CH:31][CH:30]=3)[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[N:9]2[CH2:18][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 115061,4-BenzenedimethanolHCID 513497043-(4-Chlorophenyl)-3-hydroxy-2-(4-nitrobenzyl)isoindolin-1-one

Product 1

HCID 513505153-(4-Chlorophenyl)-3-(4-hydroxymethylbenzyloxy)-2-(4-nitrobenzyl)-2,3-dihydroisoindol-1-oneYield 78%

Procedure

The named compound was synthesised from 3-(4-chlorophenyl)-3-hydroxy-2-(4-nitrobenzyl)-2,3-dihydroisoindol-1-one (541 mg, 1.37 mmol, 1 equiv.) and 1,4-benzenedimethanol (946 mg, 6.85 mmol, 5 equiv.) using General Procedure A and obtained as a white solid (405 mg, 78%). 1H NMR (300 MHz, CDCl3): 8.01-7.85 (m, 3H, O2N—C—CH and C(O)═C═CH), 7.61-7.53 (m, 2H, Ar—H), 7.37-7.18 (m, 9H, Ar—H), 6.93 (d, J=7.8 Hz, 2H, Ar—H), 4.85 and 4.67 (d: AB, J=15.0 Hz, 2H, N—CH2), 4.66 (d, J=5.7 Hz, CH2—OH), 3.90 and 3.68 (d: AB, J=11.7 Hz, 2H, OCH2), 2.12 (t, J=6.0 Hz, 1H, OH). 13C NMR (75 MHz, CDCl3): 168.52, 147.63, 145.39, 144.90, 141.16, 137.34, 136.39, 135.37, 133.42, 131.73, 130.57, 130.32, 129.19, 128.38, 127.30, 127.11, 124.34, 123.69, 95.52, 65.26, 65.12, 42.89. m/z (ES): 515 [M+H]+.

Sources & evidence

ORD record
ord-4e678c9784ff4c16903b07e37da2b2c7
Source dataset
uspto-grants-2016_06
Patent number
US09358222B2

Reaction notes

Loading…