2-Butene-1,4-diol, (2Z)- → HCID 67179180, compound

HRID 1916980Notes

Reaction equation

HRID 1916980 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.[CH2:29](O)/[CH:30]=[CH:31]\[CH2:32][OH:33]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([O:28][CH2:29][CH:30]=[CH:31][CH2:32][OH:33])[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 6437902-Butene-1,4-diol, (2Z)-HCID 513497043-(4-Chlorophenyl)-3-hydroxy-2-(4-nitrobenzyl)isoindolin-1-one

Product 1

HCID 67179180HCID 67179180, compoundYield 58%

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 cis-butenediol (445 mg, 5.05 mmol, 5 equiv.) using General Procedure A and obtained as a yellow oil (272 mg, 58%). 1H NMR (300 MHz, CDCl3): 8.04-8.00 (m, 2H, O2N—C—CH), 7.93-7.91 (m, 1H, C(O)═C═CH), 7.57-7.51 (m, 2H, Ar—H), 7.39-7.36 (m, 2H, Ar—H), 7.23-7.12 (m, 5H, Ar—H), 5.62-5.53 (m, 1H, OCH2Cl), 5.35-5.26 (m, 1H, OCH2CH), 4.64 and 4.26 (dd: AB, J=15.0 Hz, 2H, N—CH2), 3.79 (d, J=6.6 Hz, HO—CH2), 3.48-3.29 (m, 2H, O—CH2). 13C NMR (75 MHz, CDCl3): 168.17, 147.45, 145.07, 144.60, 136.86, 134.98, 133.07, 132.00, 131.44, 130.24, 130.02, 128.71, 127.99, 126.79, 123.89, 123.35, 95.00, 59.20, 58.48, 42.57. m/z (ES): 465 [M+H]+. Anal.: calc. for C25H21ClN2O5: C, 64.59; H, 4.55; N, 6.02. Found: C, 64.39; H, 4.67; N, 5.67.

Sources & evidence

ORD record
ord-7ba8d5fc482f416fa90882aefda45e7c
Source dataset
uspto-grants-2013_12
Patent number
US08618158B2

Reaction notes

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