o-Iodonitrobenzene → HCID 24821366, compound

HRID 1028374Notes

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

Reactant 2

HCID 69115o-Iodonitrobenzene

HCID 74463Nicotinanilide

Product 1

HCID 24821366HCID 24821366, compoundYield 67.1%

Procedure

The title compound was prepared with the analogous procedure described in example 1 using 1-Iodo-2-nitrobenzene (125 mg, 0.5 mmol) and nicotinanilide (119 mg, 0.6 mmol) as starting materials to yield the title compound as brown solid (91 mg, 67%). mp 110-112° C. 1H NMR (DMSO) δ 7.26 (d, J=7.3 Hz, 1 H), 7.32-7.63 (m, 8 H), 7.86 (d, J=7.6 Hz, 1 H), 7.89 (d, J=7.8 Hz, 1 H), 8.62 (d, J=3.0 Hz, 1 H), 8.72 (br s, 1 H); 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.

Workup

customThe title compound was prepared with the analogous procedure

Sources & evidence

ORD record: ord-fda9c3fa4d2c40e98c3a32d27d526e63
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735586B2

Reaction notes

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