1,4-Butanediol → HCID 44595459, compound

HRID 1916987Notes

Reaction equation

HRID 1916987 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:29])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[N:9]2[CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=2)=[CH:4][CH:3]=1.[CH2:30](O)[CH2:31][CH2:32][CH2:33][OH:34]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([O:29][CH2:30][CH2:31][CH2:32][CH2:33][OH:34])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[N:9]2[CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 80641,4-ButanediolHCID 51349837HCID 51349837, compound

Product 1

HCID 44595459HCID 44595459, compoundYield 63%

Procedure

The named compound was synthesised from 3-(4-chlorophenyl)-3-hydroxy-2-[2-(4-nitrophenyl)ethyl]-2,3-dihydroisoindol-1-one (562 mg, 1.37 mmol, 1 equiv.) and 1,4-butanediol (616 mg, 6.85 mmol, 5 equiv.) using General Procedure A and obtained as a white solid (306 mg, 63%). 1H NMR (300 MHz, CDCl3): 8.11-8.08 (m, 2H, O2N—C—CH), 7.91-7.88 (m, 1H, C(O)═C═CH), 7.55-7.53 (m, 2H, Ar—H), 7.30-7.14 (m, 7H, Ar—H), 3.66 (m, 2H, N—CH2), 3.45 (t, J=8.1 Hz, 2H, HO—CH2), 3.16-3.11 and 3.03-2.99 (m, 2H, OCH2), 3.00-2.89 and 2.73-2.66 (m, 2H, NCH2CH2), 1.75-1.63 (m, 5H, CH2 and OH). 13C NMR (75 MHz, CDCl3): 168.23, 147.02, 146.62, 145.32, 137.69, 134.84, 132.74, 131.98, 129.99, 129.48, 128.74, 127.87, 123.65, 123.51, 123.10, 94.54, 62.79, 62.43, 40.51, 34.21, 29.60, 26.07. HPLC: Rt=3.45 min. calc. for C26H25ClN2O5: C, 64.93; H, 5.24; N, 5.82. Found: C, 64.82; H, 5.18; N, 5.68.

Sources & evidence

ORD record
ord-60624d3074084849bf6222eae32a7270
Source dataset
uspto-grants-2013_12
Patent number
US08618158B2

Reaction notes

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