3-Fluoroaniline → HCID 178522051, compound

HRID 749196Notes

Reaction equation

HRID 749196 reaction equation
[N+:1]([C:4]1[CH:8]=[C:7]([C:9]([OH:11])=O)[NH:6][N:5]=1)([O-:3])=[O:2].[F:12][C:13]1[CH:14]=[C:15]([CH:17]=[CH:18][CH:19]=1)[NH2:16].Cl.CN(C)CCCN=C=NCC.OC1C=CC=C[N+]=1[O-]>CN(C)C=O>[F:12][C:13]1[CH:14]=[C:15]([NH:16][C:9]([C:7]2[NH:6][N:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:8]=2)=[O:11])[CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 97423-FluoroanilineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178524578HCID 178524578, compoundHCID 178526252HCID 178526252, compound

Product 1

HCID 178522051HCID 178522051, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-nitro-1H-pyrazole-5-carboxylic acid (1 g, 6.36 mmol) in dimethylformamide (10 ml) was reacted with 3-fluoroaniline (673 μl, 7 mmol) in the presence of 1-(3-dimethylamino-propyl)-3-ethylcarbodiimide hydrochloride (1.34 g, 7 mmol) and 2-hydroxy-pyridin-1-oxide (778 mg, 7 mmol) at 40° C. for 1.5 hour. The solvent was evaporated, and the residue purified by chromatography on silica gel. Elution with dichloromethane:methanol (99:1) then (97:3) yielded N-(3-fluorophenyl)-3-nitro-1H-pyrazole-5-carboxamide (668 mg, 42% yield):

Workup

  1. customThe solvent was evaporated
  2. customthe residue purified by chromatography on silica gel
  3. washElution with dichloromethane:methanol (99:1)

Sources & evidence

ORD record
ord-cb69a7bc170f42979bfb18d4d2f790a4
Source dataset
uspto-grants-2008_07
Patent number
US07402585B2

Reaction notes

Loading…