Citric Acid → 4-(5-Iodoindazole-1-yl)-benzoic acid

HRID 1098900

反応式

HRID 1098900 の反応式
[NH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)[NH2:2].C(=O)([O-])[O-].[Cs+].[Cs+].F[C:19]1[CH:26]=[CH:25][C:24]([I:27])=[CH:23][C:20]=1[CH:21]=O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN1CCCC1=O>[I:27][C:24]1[CH:23]=[C:20]2[C:19](=[CH:26][CH:25]=1)[N:1]([C:3]1[CH:4]=[CH:5][C:6]([C:7]([OH:9])=[O:8])=[CH:10][CH:11]=1)[N:2]=[CH:21]2

参加物

6

反応物 4

HCID 311Citric AcidHCID 10796Cesium carbonateHCID 120894-Hydrazinobenzoic acidHCID 162170582-Fluoro-5-iodobenzaldehyde

生成物 1

HCID 593397454-(5-Iodoindazole-1-yl)-benzoic acid収率 78.32%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

4-Hydrazinobenzoic acid (11.32 g, 60 mmol) and cesiumcarbonate (58.65 g, 180 mmol) are added to 2-fluoro-5-iodobenzaldehyde (15 g, 60 mmol) in 300 mL N-methylpyrrolidon. After 1 h stirring at r.t., the reaction is heated for 4 h at 150° C. The reaction mixture is allowed to cool off and poured on 1 L ice water. The reaction mixture is acidified with citric acid and vigorously stirred at r.t. for 30 min. The precipitate is filtered off and given in ethyl acetate. The slurry is vigorously stirred for 1 h and sucked off. The filter residue (few material) is discarded and the filtrate evaporated. This residue which is contaminated with N-methylpyrrolidine is treated with 300 mL of a mixture of ethyl acetate/hexane (1:3) and stirred overnight. The precipitated crystals are sucked off and dried. 17.11 g (78.32%) of 4-(5-iodoindazole-1-yl)-benzoic acid are obtained.

後処理

  1. temperaturethe reaction is heated for 4 h at 150° C
  2. temperatureto cool off
  3. stirringvigorously stirred at r.t. for 30 min
  4. filtrationThe precipitate is filtered off
  5. stirringThe slurry is vigorously stirred for 1 h
  6. customthe filtrate evaporated
  7. additionis treated with 300 mL of a mixture of ethyl acetate/hexane (1:3)
  8. stirringstirred overnight
  9. customdried

出典と根拠

ORDレコード
ord-449b478386e94682a8ae5fca621a1c9d
出典データセット
uspto-grants-2012_03
特許番号
US08143290B2

関連ノート

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