Sodium Hydroxide → 5-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-4-amine

HRID 406581Notes

Reaction equation

HRID 406581 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:13]([CH3:14])[N:12]=[C:11]([CH3:15])[C:10]=1[NH:16]C(=O)[O-].ClC1C=C(F)C=CC=1C1N(C)N=C(C)C=1NC(=O)OC.[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:13]([CH3:14])[N:12]=[C:11]([CH3:15])[C:10]=1[NH2:16]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 66613601methyl N-[5-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-4-yl]carbamateHCID 86686302N-[5-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-4-yl]carbamate

Product 1

HCID 666133695-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-4-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of N-[5-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-4-yl]carbamate (i.e. the product of Step E) (7.07 g, 23.8 mmol) and aqueous sodium hydroxide (1 N, 70 mL) in methanol (70 mL) was heated at reflux for 20 h. The reaction mixture was concentrated under reduced pressure, diluted with water and extracted with ethyl acetate (2×30 mL). The combined organic layers were extracted with hydrochloric acid (1 N, 2×30 mL), and the pH of the combined aqueous extracts was adjusted to 10 with the addition of sodium hydroxide (1 N). The aqueous mixture was extracted with ethyl acetate (2×40 mL). The combined organic extracts were washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered and concentrated under reduced pressure to provide the title compound as a viscous yellow oil (4.36 g).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 20 h
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additiondiluted with water
  5. extractionextracted with ethyl acetate (2×30 mL)
  6. extractionThe combined organic layers were extracted with hydrochloric acid (1 N, 2×30 mL)
  7. additionthe pH of the combined aqueous extracts was adjusted to 10 with the addition of sodium hydroxide (1 N)
  8. extractionThe aqueous mixture was extracted with ethyl acetate (2×40 mL)
  9. washThe combined organic extracts were washed with saturated aqueous sodium chloride solution
  10. dry with materialdried over magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-63893b8adfa040108083935da7bb9328
Source dataset
uspto-grants-2014_06
Patent number
US08754115B2

Reaction notes

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