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

HRID 2276009

反応式

HRID 2276009 の反応式
[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]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66614282methyl 5-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-4-carboxylate2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-396017ac24734bf7a5ee199a66275d1f
出典データセット
uspto-grants-2015_09
特許番号
US09131693B2

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