o-Iodonitrobenzene → HCID 24821369, compound

HRID 1931271Notes

Reaction equation

I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-])=O.[CH3:11][O:12][C:13](=[O:27])[CH2:14][CH2:15][CH2:16][CH2:17][C:18](=O)[NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[CH3:11][O:12][C:13](=[O:27])[CH2:14][CH2:15][CH2:16][CH2:17][C:18]1[N:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:2]=2)[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[N:19]=1

Participants

Reactant 2

HCID 69115o-Iodonitrobenzene

HCID 114817425-phenylcarbamoyl-pentanoic acid methyl ester

Product 1

HCID 24821369HCID 24821369, compoundYield 88.2%

Procedure

Method A applied to 1-iodo-2-nitrobenzene (125 mg, 0.5 mmol) and 5-phenylcarbamoyl-pentanoic acid methyl ester (141 mg, 0.6 mmol) yielded the title compound as brown oil (136 mg, 88%). 1H NMR (DMSO) δ 1.50-1.74 (m, 4H), 2.27 (d, J=7.2Hz, 2H), 2.89 (d, J=7.5Hz, 2H), 3.52 (s, 3H), 7.22 (d, J=8.1Hz, 1H), 7.38 (apparent t, J=7.6Hz, 1H), 7.46 (apparent t, J=7.6Hz, 1H), 7.52-7.72 (m, 5H), 7.79 (d, J=7.8 Hz, 1H); 13C NMR δ 23.3, 25.3, 25.4, 32.2, 50.9, 111.3, 115.6, 124.3, 124.4, 126.8, 130.0, 132.4, 133.2, 133.4, 153.9, 172.3. HRMS (FAB): cal. for C19H21N2O2 [M+H+]: 309.1603; found: 309.1595.

Sources & evidence

ORD record: ord-a3d18755df2e45249902e698b7bfdd99
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188282B2

Reaction notes

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