Sodium Hydroxide → 5-(4-Fluorophenyl)-1-(6-methoxy-3-pyridyl)pyrazole-3-carboxylic acid

HRID 1437255ノート

反応式

HRID 1437255 の反応式
[OH-].[Na+].C([O:5][C:6]([C:8]1[CH:12]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[N:10]([C:20]2[CH:21]=[N:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=2)[N:9]=1)=[O:7])C>CO>[F:19][C:16]1[CH:17]=[CH:18][C:13]([C:11]2[N:10]([C:20]3[CH:21]=[N:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=3)[N:9]=[C:8]([C:6]([OH:7])=[O:5])[CH:12]=2)=[CH:14][CH:15]=1

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 579406805-(4-Fluorophenyl)-1-(6-methoxy-3-pyridyl)pyrazole-3-carboxylic acid ethyl ester

生成物 1

HCID 230904085-(4-Fluorophenyl)-1-(6-methoxy-3-pyridyl)pyrazole-3-carboxylic acid収率 88%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Aqueous 1N sodium hydroxide (1.2 L) was added to 5-(4-fluorophenyl)-1-(6-methoxy-3-pyridyl)pyrazole-3-carboxylic acid ethyl ester (164 g) in methanol (1.6 L), and the resultant mixture was stirred at room temperature for 5 hours. The reaction solvent was removed under reduced pressure, and the residue was partitioned between water and diethyl ether. The aqueous layer was adjusted at pH 2 through addition of aqueous 1N hydrochloric acid (1.5 L), and the precipitated crystals were dissolved in chloroform. The resultant solution was partitioned by use of saturated brine, and the organic layer was dried over sodium sulfate anhydrate, followed by filtration. The solvent was evaporated under reduced pressure, and the precipitated crystals from diethyl ether were recovered by filtration, to thereby give the title compound (132.0 g, 88%).

後処理

  1. customThe reaction solvent was removed under reduced pressure
  2. customthe residue was partitioned between water and diethyl ether
  3. additionThe aqueous layer was adjusted at pH 2 through addition of aqueous 1N hydrochloric acid (1.5 L)
  4. dissolutionthe precipitated crystals were dissolved in chloroform
  5. customThe resultant solution was partitioned by use of saturated brine
  6. dry with materialthe organic layer was dried over sodium sulfate anhydrate
  7. filtrationfollowed by filtration
  8. customThe solvent was evaporated under reduced pressure
  9. filtrationthe precipitated crystals from diethyl ether were recovered by filtration

出典と根拠

ORDレコード
ord-5af91f7dd39b417bbec58d5fd75312c4
出典データセット
uspto-grants-2009_11
特許番号
US07622471B2

反応ノート

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