o-Iodonitrobenzene → HCID 24821366, compound

HRID 1931267Notes

Reaction equation

HRID 1931267 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-])=O.[C:11]([NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(=O)[C:12]1[CH:17]=[CH:16][CH:15]=[N:14][CH:13]=1>>[C:3]1([N:8]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[N:19]=[C:11]2[C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:2]=1

Participants

3

Reactant 2

HCID 69115o-IodonitrobenzeneHCID 74463Nicotinanilide

Product 1

HCID 24821366HCID 24821366, compoundYield 50.1%

Procedure

Method A applied to 1-iodo-2-nitrobenzene (125 mg, 0.5 mmol) and nicotinanilide (119 mg, 0.6 mmol) yielded the title compound as brown solid (68 mg, 50%). mp 110-112° C. 1H NMR (DMSO) δ 7.26 (d, J=7.3Hz, 1H), 7.32-7.63 (m, 8H), 7.86 (d, J=7.6 Hz, 1H), 7.89 (d, J=7.8Hz, 1H), 8.62 (d, J=3.0Hz, 1H), 8.72 (br s, 1H); 13C NMR δ 111.0, 118.7, 123.8, 124.0, 124.4, 125.4, 127.6, 129.5, 130.2, 135.2, 136.4, 137.7, 140.3, 148.6, 149.6, 158.3. HRMS (FAB): cal. for C18H14N3 [M+H+]: 272.1188; found: 272.1180.

Sources & evidence

ORD record
ord-279117aa58bc4760b3cf107c5ef83e21
Source dataset
uspto-grants-2012_05
Patent number
US08188282B2

Reaction notes

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