3-(4-Chlorophenyl)-3-hydroxy-2-(4-nitrobenzyl)isoindolin-1-one → 3-(4-Chlorophenyl)-3-(4-hydroxymethylcyclohexylmethoxy)-2-(4-nitrobenzyl)-2,3-dihydroisoindol-1-one

HRID 2199294Notes

Reaction equation

HRID 2199294 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@H:29]1([CH2:37]O)[CH2:34][CH2:33][C@H:32]([CH2:35][OH:36])[CH2:31][CH2:30]1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([O:28][CH2:37][CH:29]3[CH2:34][CH2:33][CH:32]([CH2:35][OH:36])[CH2:31][CH2:30]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 513497043-(4-Chlorophenyl)-3-hydroxy-2-(4-nitrobenzyl)isoindolin-1-oneHCID 178520956HCID 178520956, compound

Product 1

HCID 513505163-(4-Chlorophenyl)-3-(4-hydroxymethylcyclohexylmethoxy)-2-(4-nitrobenzyl)-2,3-dihydroisoindol-1-oneYield 71.1%

Procedure

The named compound was synthesised from 3-(4-Chlorophenyl)-3-hydroxy-2-(4-nitrobenzyl)-2,3-dihydroisoindol-1-one (400 mg, 1.01 mmol, 1 equiv.) and trans-cyclohexane-1,4-dimethanol (728 mg, 5.05 mmol, 5 equiv.) using General Procedure A and obtained as a yellow solid (374 mg, 71%). 1H NMR (300 MHz, CDCl3): 8.05-7.92 (m, 3H, O2N—C—CH and C(O)═C═CH), 7.56-7.53 (m, 2H, Ar—H), 7.38-7.10 (m, 7H, Ar—H), 4.59 and 4.35 (d: AB, J=15.0 Hz, 2H, N—CH2), 3.44 (d, J=6.3 Hz, 2H, HO—CH2), 2.65-2.53 (m, 2H, OCH2), 1.81-1.74 (m, 3H, OH and CH), 1.44-1.32 (m, 2H), 0.93-0.79 (m, 5H). 13C NMR (75 MHz, CDCl3): 168.26, 145.41, 144.82, 137.42, 134.84, 132.93, 130.01, 128.63, 128.01, 123.80, 123.24, 123.18, 94.67, 68.41, 68.26, 42.41, 40.59, 38.04, 29.68, 29.31, 28.90. m/z (ES): 521 [M+H]+. Anal.: calc. for C29H29ClN2O5+0.2 H2O: C, 66.38; H, 5.66; N, 5.34. Found: C, 66.23; H, 5.79; N, 4.99.

Sources & evidence

ORD record
ord-1f9c69eeb7db49efb407cb79979445c5
Source dataset
uspto-grants-2016_06
Patent number
US09358222B2

Reaction notes

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