Chlorine → 5-(5-Chloro-3-fluoro-2-pyridyl)-4-chloro-2-methyl-[2h]-pyrazole-3-carboxylic acid ethyl ester

HRID 650487Notes

Reaction equation

HRID 650487 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:19])[N:8]=[C:9]([C:11]2[C:16]([F:17])=[CH:15][C:14]([Cl:18])=[CH:13][N:12]=2)[CH:10]=1)=[O:5])[CH3:2].C([O-])(=O)C.[Na+].[Cl:25]Cl>C(O)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:19])[N:8]=[C:9]([C:11]2[C:16]([F:17])=[CH:15][C:14]([Cl:18])=[CH:13][N:12]=2)[C:10]=1[Cl:25])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 24526ChlorineHCID 517045Sodium AcetateHCID 220135663-(3-Fluoro-5-chloro-2-pyridyl)-5-ethoxycarbonyl-1-methyl-[1H]-pyrazole

Product 1

HCID 206773465-(5-Chloro-3-fluoro-2-pyridyl)-4-chloro-2-methyl-[2h]-pyrazole-3-carboxylic acid ethyl esterYield 95%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

22.9 g of 5-(5-chloro-3-fluoro-2-pyridyl)-2-methyl-[2H]-pyrazole-3-carboxylic acid ethyl ester (Example P19) are introduced together with 19.9 g of sodium acetate into 300 ml of glacial acetic acid at a temperature of 65° C. With stirring, 6.3 g of chlorine gas are passed over the solution at that temperature in the course of 1 hour. The reaction mixture is then poured into 2.5 liters of ice-water and subsequently stirred for 20 minutes. The resulting precipitate is filtered off, washed with ice-water and then dried in vacuo at 50° C. 24.4 g of the desired title compound are obtained in the form of a yellow solid having a melting point of 77-79° C.

Workup

  1. customare passed over the solution at that temperature in the course of 1 hour
  2. stirringsubsequently stirred for 20 minutes
  3. filtrationThe resulting precipitate is filtered off
  4. washwashed with ice-water
  5. customdried in vacuo at 50° C

Sources & evidence

ORD record
ord-ab5ad496f1ca48fd9d431eeedf72a0a8
Source dataset
uspto-grants-2001_08
Patent number
US06274536B1

Reaction notes

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