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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1916982Generated: October 26, 2026

1,1-Bis(hydroxymethyl)cyclopropane → 3-(4-Chlorophenyl)-3-(1-hydroxymethylcyclopropylmethoxy)-2-(4-nitrobenzyl)-2,3-dihydroisoindol-1-one

https://huagongshe.com/reaction/1916982

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1,1-Bis(hydroxymethyl)cyclopropaneHCID 4101437—
Reactant3-(4-Chlorophenyl)-3-hydroxy-2-(4-nitrobenzyl)isoindolin-1-oneHCID 51349704—
Product3-(4-Chlorophenyl)-3-(1-hydroxymethylcyclopropylmethoxy)-2-(4-nitrobenzyl)-2,3-dihydroisoindol-1-oneHCID 5331852063.1%

Reaction Steps

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 cyclopropane dimethanol (516 mg, 5.05 mmol, 5 equiv.) using General Procedure A and obtained as an off-white solid (305 mg, 63%). 1H NMR (300 MHz, CDCl3): 8.01-7.98 (m, 2H, O2N—C—CH), 7.92-7.89 (m, 1H, C(O)═C═CH), 7.55-7.52 (m, 2H, Ar—H), 7.32-7.29 (m, 2H, Ar—H), 7.19-7.12 (m, 5H, Ar—H), 4.49 (s, 2H, N—CH2), 3.51-3.43 (m, 2H, HOCH2), 2.81 (s, 2H, OCH2), 0.43-0.40 (m, 2H, CH2), 0.22-0.12 (m, 2H, CH2). 13C NMR (75 MHz, CDCl3): 168.54, 145.52, 144.95, 137.47, 135.29, 133.45, 131.87, 130.50, 130.21, 128.98, 128.30, 124.16, 123.60, 123.48, 94.96, 67.84, 42.75, 22.68, 8.94, 8.90 Anal.: calc. for C26H23ClN2O5: C, 65.20; H, 4.84; N, 5.85, Found: C, 64.83; H, 4.92; N, 5.63.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08618158B2
Source datasetuspto-grants-2013_12
ORD IDord-d964c2251f1c4548b22a686bdbc24ce5
Source noteuspto-grants-2013_12