3-Nitroaniline → HCID 178441944, compound

HRID 2095164Notes

Reaction equation

[CH2:1]([C:5]1[C:6](=[N:11][NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+]([O-])=O)[CH:14]=2)[C:7]([NH2:10])=[N:8][N:9]=1)[CH2:2][CH:3]=[CH2:4].[N+:22]([C:25]1C=C(C=[CH:30][CH:31]=1)N)([O-])=O.C(CC(=O)CCC=C)#N.CC([O-])=O.[Na+]>>[CH2:1]([C:5]1[C:6](=[N:11][NH:12][C:13]2[CH:14]=[C:15]3[C:16](=[CH:17][CH:18]=2)[N:22]=[CH:25][CH:31]=[CH:30]3)[C:7]([NH2:10])=[N:8][N:9]=1)[CH2:2][CH:3]=[CH2:4]

Participants

Reactant 4

HCID 74233-Nitroaniline

HCID 517045Sodium Acetate

HCID 24975800HCID 24975800, compound

HCID 178441946HCID 178441946, compound

Product 1

HCID 178441944HCID 178441944, compoundYield 61%

Procedure

In a similar manner, 5-but-3-enyl-4-[(3-nitrophenyl)hydrazono]4H-pyrazol-3-ylamine was prepared from 3-nitroaniline (166 mg, 1.2 mmole) and 1-cyano-5-hexen-2-one (123 mg, 1 mmole) with NaOAc (979 mg, 7.2 mmole) according to a procedure similar to Example 2. The crude material was purified by a prepreparative TLC (CH2Cl2:MeOH=21:1) to yield 175 mg (61%) of the title compound as an orange powder. MS (m/z, ES+): 287 (M+1, 100%); 1H NMR (ppm, 300 MHz, DMSO-d6-CDCl3) δ 11.60 (br s, 1H), 8.38 (s, 1H), 7.99 (m, 1H), 7.57 (t, 1H), 6.64 (br s, 2H), 5.84 (m, 1H), 5.03 (d, 1H), 4.92 (d, 1H), 2.88 (m, 2H), 2.48 (m, 2H).

Workup

customThe crude material was purified by a prepreparative TLC (CH2Cl2:MeOH=21:1)

Sources & evidence

ORD record: ord-97ecf360694f449282b04dbc14387357
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445694B2

Reaction notes

Loading…