Ammonia → 2-Nitro-5-(3-(pyridin-3-yl)-1,2,4-oxadiazol-5-yl)phenol

HRID 450697Notes

Reaction equation

HRID 450697 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([OH:7])=O.O[N:15]=[C:16]([NH2:23])[C:17]1[CH:22]=[CH:21][CH:20]=[N:19][CH:18]=1.N>>[N+:11]([C:10]1[CH:9]=[CH:8][C:4]([C:5]2[O:7][N:23]=[C:16]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[N:15]=2)=[CH:3][C:2]=1[OH:1])([O-:13])=[O:12]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 692653-Hydroxy-4-nitrobenzoic acidHCID 308113N-Hydroxynicotinimidamide

Product 1

HCID 670260952-Nitro-5-(3-(pyridin-3-yl)-1,2,4-oxadiazol-5-yl)phenol

Procedure

The title compound was prepared according to Method C using 3-hydroxy-4-nitrobenzoic acid (Aldrich) and N′-hydroxynicotinimidamide (Tyger). 1H NMR (300 MHz, DMSO-d6) δ 7.67 (ddd, J=7.9, 4.8, 0.8 Hz, 1 H), 7.76 (dd, J=8.5, 1.8 Hz, 1 H), 7.92 (d, J=1.6 Hz, 1 H), 8.12 (d, J=8.3 Hz, 1 H), 8.45 (dt, J=7.9, 2.0 Hz, 1 H), 8.83 (dd, J=4.8, 1.6 Hz, 1 H), 9.26 (d, J=1.2 Hz, 1 H)) ppm; MS (DCI/NH3) m/z 285 (M+H)+.

Sources & evidence

ORD record
ord-e5a68e1c1b75456c94eb275b3a44f315
Source dataset
uspto-grants-2013_07
Patent number
US08486979B2

Reaction notes

Loading…