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

HRID 578104Notes

Reaction equation

[OH:1][N:2]=[C:3]([NH2:10])[C:4]1[CH:9]=[CH:8][CH:7]=[N:6][CH:5]=1.[OH:11][C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][C:20]=1[N+:21]([O-:23])=[O:22])[C:15](O)=O.N>>[N+:21]([C:20]1[CH:19]=[CH:18][C:14]([C:15]2[O:1][N:2]=[C:3]([C:4]3[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=3)[N:10]=2)=[CH:13][C:12]=1[OH:11])([O-:23])=[O:22]

Participants

Reactant 3

HCID 222Ammonia

HCID 692653-Hydroxy-4-nitrobenzoic acid

HCID 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 the procedure of Example 8 using N′-hydroxynicotinimidamide (Aldrich) and 3-hydroxy-4-nitrobenzoic acid (Maybridge). 1H NMR (300 MHz, DMSO-d6) δ 6.51 (d, J=9.1 Hz, 1H), 6.92-7.31 (s (broad), 1H), 7.61 (ddd, J=7.9, 4.8, 0.8 Hz, 1H), 7.68 (dd, J=9.1, 2.4 Hz, 1H), 8.40 (dt, J=7.9, 2.0 Hz, 1H), 8.53 (d, J=2.4 Hz, 1H), 8.77 (dd, J=4.8, 1.6 Hz, 1H), 9.20 (d, J=1.6 Hz, 1H) ppm; MS (DCI/NH3) m/z 285 (M+H)+.

Sources & evidence

ORD record: ord-ff8486e1d7e34c3aa6a7c462154442db
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040568B2

Reaction notes

Loading…