But-2-yne-1,1-diol → 3-(4-Chlorophenyl)-3-(4-hydroxybut-2-ynyloxy)-2-(4-nitrobenzyl)-2,3 dihydroisoindol-1-one

HRID 1916983Notes

Reaction equation

HRID 1916983 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.[CH:29](O)([OH:33])[C:30]#[C:31][CH3:32]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([O:28][CH2:32][C:31]#[C:30][CH2:29][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 18778928But-2-yne-1,1-diolHCID 513497043-(4-Chlorophenyl)-3-hydroxy-2-(4-nitrobenzyl)isoindolin-1-one

Product 1

HCID 445956063-(4-Chlorophenyl)-3-(4-hydroxybut-2-ynyloxy)-2-(4-nitrobenzyl)-2,3 dihydroisoindol-1-oneYield 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 butynediol (435 mg, 5.05 mmol, 5 equiv.) using General Procedure A and obtained as a yellow solid (271 mg, 58%). 1H NMR (300 MHz, CDCl3): 8.05-7.93 (m, 3H, O2N—C—CH and C(O)═C═CH), 7.61-7.54 (m, 2H, Ar—H), 7.36-7.33 (m, 2H, Ar—H), 7.24-7.16 (m, 5H, Ar—H), 4.60 and 4.52 (d: AB, J=15.0 Hz, 2H, N—CH2), 4.20-4.18 (m, 2H, HO—CH2), 3.83 and 3.52 (dt: AB, J=1.8, 15.3 Hz, 2H, O—CH2), 2.42 (t, J=6.0 Hz, 1H, OH). 13C NMR (75 MHz, CDCl3): 169.24, 148.20, 145.18, 137.24, 135.88, 133.78, 132.49, 131.29, 130.78, 129.43, 128.79, 124.81, 124.43, 124.14, 95.88, 86.01, 81.28, 54.04, 52.97, 51.55, 43.60. m/z (ES): 463 [M+H]+. calc. for C25H19ClN2O5+0.2 H2O: C, 64.36; H, 4.20; N, 6.01. Found: C, 64.11; H, 3.72; N, 5.53.

Sources & evidence

ORD record
ord-438965fd854544668f5ecaaadc1c0f74
Source dataset
uspto-grants-2013_12
Patent number
US08618158B2

Reaction notes

Loading…