Isonicotinic Acid → N-(3-nitrophenyl)isonicotinamide

HRID 64245Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7])([O-:3])=[O:2].[C:11](O)(=[O:18])[C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1>>[N+:1]([C:4]1[CH:5]=[C:6]([NH:7][C:11](=[O:18])[C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[CH:8]=[CH:9][CH:10]=1)([O-:3])=[O:2]

Participants

Reactant 2

HCID 5922Isonicotinic Acid

HCID 74233-Nitroaniline

Product 1

HCID 790430N-(3-nitrophenyl)isonicotinamide

Procedure

The general procedure for 8 was followed using 3-nitro aniline 31 and isonicotinic acid to afforded (68%) as a yellow solid. 1H NMR (DMSO-d6, 400 MHz) δ 7.67-7.71 (m, 1H), 7.89-7.91 (m, 2H), 8.01 (dd, J, =8.4 Hz, J2=1.6 Hz, 1H), 8.19 (dd, J, =8 Hz, J2=1.6 Hz, 1H), 8.79-8.83 (m, 3H), 10.9 (NH, s, 1H).

Workup

customto afforded (68%) as a yellow solid

Sources & evidence

ORD record: ord-1c2729b44194419fb2ac3e8fbe0ef614
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447134B2

Reaction notes

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