Methanol → HCID 21188125, compound

HRID 1383570Notes

Reaction equation

HRID 1383570 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]#[N:20])[C:3]=1[C:21]#[C:22][CH2:23][OH:24].[CH3:25][OH:26].[C-]#N.[K+]>CCOCC.[O-2].[O-2].[Mn+4]>[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:16])([F:15])[F:17])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]#[N:20])[C:3]=1[C:21]#[C:22][C:23]([O:26][CH3:25])=[O:24]

Participants

6

Reactant 3

HCID 887MethanolHCID 9032Potassium CyanideHCID 21188055HCID 21188055, compound2×

Product 1

HCID 21188125HCID 21188125, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)4-(3-hydroxyprop-1-ynyl)pyrazole (250 mg, the compound of Example A6) in ether (10 ml) was added manganese dioxide (1 g) and the mixture stirred at room temperature for two hours. Methanol (2 ml) and potassium cyanide (250 mg) were then added and stirring continued for 15 minutes. The reaction mixture was filtered and evaporated to dryness. The residue was purified by chromatography on silica gel eluted with dichloromethane. Combination and evaporation of appropriate fractions provided the title compound as a light brown solid m.p. 201-2° C.

Workup

  1. stirringstirring
  2. waitcontinued for 15 minutes
  3. filtrationThe reaction mixture was filtered
  4. customevaporated to dryness
  5. customThe residue was purified by chromatography on silica gel
  6. washeluted with dichloromethane
  7. customCombination and evaporation of appropriate fractions

Sources & evidence

ORD record
ord-b5033eb70fc54253bf5f7a5f7740f138
Source dataset
uspto-grants-2001_07
Patent number
US06255333B1

Reaction notes

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