4-Fluoroaniline → HCID 12985694, compound

HRID 2119615

Reaction equation

HRID 2119615 reaction equation
I[C:2]1[CH:3]=[N:4][N:5]([CH3:10])[C:6]=1[C:7](O)=[O:8].[F:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Na+].[Na+].[OH-].[Na+]>[Cu].C(OCC)C>[F:11][C:12]1[CH:18]=[CH:17][C:15]2[NH:16][C:2]3[CH:3]=[N:4][N:5]([CH3:10])[C:6]=3[C:7](=[O:8])[C:14]=2[CH:13]=1

Participants

7

Reactant 4

HCID 97314-FluoroanilineHCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 6736874-Iodo-1-methyl-1H-pyrazole-5-carboxylic acid

Product 1

HCID 12985694HCID 12985694, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 4-iodo-1-methyl-1H-pyrazole-5-carboxylic acid ((Manaev, Yu. A. et al., J. Gen. Chem. USSR (Engl. Transl.), 1982, 52 (11), 2291), 500 mg, 1.98 mmol), 4-fluoroaniline (0.94 ml, 9.90 mmol), copper powder (200 mg) and 5% aqueous sodium carbonate (10 ml) was stirred for 16 h at 100° C. After cooling to room temperature, 2N aqueous sodium hydroxide (100 ml) and diethyl ether (50 ml) were added to the mixture. The mixture was filtered through a pad of Celite. The water layer was separated, washed with diethyl ether (50 ml) and acidified with concentrated hydrochloric acid. The formed precipitate was collected by filtration and dried to give 282 mg (61%) of the title compound as a white solid.

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. customThe water layer was separated
  3. washwashed with diethyl ether (50 ml)
  4. filtrationThe formed precipitate was collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-61298bab12dd4f30a5a7fed1e8a287bf
Source dataset
uspto-grants-2004_02
Patent number
US06686373B2

Linked notes

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