Triethylamine → 3-(4-Chlorophenyl)-3-hydroxy-2-(4-nitrobenzyl)isoindolin-1-one

HRID 2381579Notes

Reaction equation

HRID 2381579 reaction equation
Cl[C:2]1([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[O:3]1.Cl.[N+:20]([C:23]1[CH:30]=[CH:29][C:26]([CH2:27][NH2:28])=[CH:25][CH:24]=1)([O-:22])=[O:21].C(N(CC)CC)C>>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([C:2]2([OH:3])[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:4](=[O:11])[N:28]2[CH2:27][C:26]2[CH:25]=[CH:24][C:23]([N+:20]([O-:22])=[O:21])=[CH:30][CH:29]=2)=[CH:13][CH:14]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 112524674-Nitrobenzylamine hydrochlorideHCID 126920383-Chloro-3-(4-chlorophenyl)-2-benzofuran-1(3H)-one

Product 1

HCID 513497043-(4-Chlorophenyl)-3-hydroxy-2-(4-nitrobenzyl)isoindolin-1-oneYield 65%

Procedure

Distilled THF (25 mL) was added to 3-chloro-3-(4-chlorophenyl)-3H-isobenzofuran-1-one (3.2 g, 11.5 mmol) followed by 4-nitrobenzylamine hydrochloride (2.3 g, 12.6 mmol) and triethylamine (4.8 mL, 34.5 mmol) as for general procedure A. The crude product was recrystallised in the minimum amount of boiling ethyl acetate to give 3-(4-chlorophenyl)-3-hydroxy-2-(4-nitrobenzyl)-2,3-dihydroisoindol-1-one as a light yellow solid (2.95 g, 7.47 mmol, 65%); Rf=0.4 (40:60:EtOAc:petrol). 197.1-199.7° C. λmax (CH3OH)/nm 220, Abs 0.765. IR: 3215, 1676, 1517, 1395, 1341 cm−1. 1H NMR: (300 MHz, d6-DMSO) δ 4.35 (d, 1H, J=16.3 Hz, N—CH2), 4.61 (d, 1H, J=16.3 Hz, N—CH2), 7.28 (m, 4H, Ar—H), 7.45 (m, 3H, Ar—H), 7.58 (m, 2H, Ar—H), 7.79 (m, 1H, Ar—H), 8.05 (m, 2H, Ar—H). 13C NMR: (75 MHz, d6-DMSO) δ 42.1, 90.5, 123.1, 123.3, 128.4, 128.7, 129.1, 129.9, 130.3, 133.2, 133.3, 138.9, 146.4, 146.5, 149.4, 167.1. LC/MS-ES+ m/z 307.2, 368.2, 377.1. Anal. Calcd. for C21H15CN2O4: C, 63.89; H, 3.83; N, 7.10%. Found C, 63.78; H, 3.92; N, 7.12%. HRMS (EI) m/z Calcd. for C21H15ClN2O4: 394.0720. Found 394.0714.

Workup

  1. distillationDistilled THF (25 mL)
  2. customThe crude product was recrystallised in the minimum amount of boiling ethyl acetate

Sources & evidence

ORD record
ord-9f370da018774fe9a5346a638849db08
Source dataset
uspto-grants-2012_09
Patent number
US08258175B2

Reaction notes

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