Hydrochloric Acid → 5-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-4-carboxylic acid

HRID 2276009노트

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HRID 2276009 반응식
[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[C:16]([O:18]C)=[O:17].[OH-].[Na+].Cl>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[C:16]([OH:18])=[O:17]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66614282methyl 5-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-4-carboxylate2회

생성물 1

HCID 666140305-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-4-carboxylic acid

시약·촉매·용매 1

HCID 887Methanol용매

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온도
0 °C

실험 절차

A mixture of methyl 5-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-4-carboxylate (i.e. the product of Step C) (12.33 g, 43.7 mol) and sodium hydroxide (1 N, 70 mL) in methanol (70 mL) was heated at reflux for 2 h. The reaction mixture was cooled to about 0° C., and then the pH of the reaction mixture was adjusted to 3 by the addition of aqueous hydrochloric acid solution (1 N). The reaction mixture was extracted with ethyl acetate (3×70 mL) and the combined extracts were washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to provide the title compound as a white solid (11.14 g).

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. extractionThe reaction mixture was extracted with ethyl acetate (3×70 mL)
  4. washthe combined extracts were washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-396017ac24734bf7a5ee199a66275d1f
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09131693B2

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