3-(Trifluoromethyl)aniline → HCID 178501727、化合物

HRID 1407075ノート

反応式

HRID 1407075 の反応式
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6].[N:12]([O-])=O.[Na+].[C:16]([O:22][CH3:23])(=[O:21])[CH2:17][C:18]([CH3:20])=[O:19].C([O-])(=O)C.[Na+]>Cl.O.C(O)C>[O:19]=[C:18]([CH3:20])[C:17](=[N:12][NH:6][C:5]1[CH:7]=[CH:8][CH:9]=[C:3]([C:2]([F:10])([F:11])[F:1])[CH:4]=1)[C:16]([O:22][CH3:23])=[O:21]

参加物

8

反応物 4

HCID 73753-(Trifluoromethyl)anilineHCID 7757Methyl acetoacetateHCID 517045Sodium AcetateHCID 23668193Sodium Nitrite

生成物 1

HCID 178501727HCID 178501727、化合物収率 69.4%

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid溶媒HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

A slurry of 3-(trifluoromethyl)aniline (16.12 g, 100 mmol) in 6 N HCl (100 mL) was cooled to 0° C. and treated dropwise with a solution of sodium nitrite (8.33 g, 121 mmol) in water (20 mL). The resulting pale yellow solution was poured into a slurry of methyl acetoacetate (11.62 g, 100 mmol) and sodium acetate (150 g) in ethanol (170 mL), pre-cooled to 0° C. The resulting orange slurry was stirred for 10 min. After that time, the product was collected by filtration and washed with water (500 mL). The crude material was dissolved in ethyl acetate (250 mL) and dried (MgSO4). The product crystallized upon concentration of the ethyl acetate to give 19.997 g (69%) of methyl 3-oxo-2-{[3-(trifluoromethyl)phenyl]hydrazono}butanoate as light yellow crystals.

後処理

  1. filtrationAfter that time, the product was collected by filtration
  2. washwashed with water (500 mL)
  3. dissolutionThe crude material was dissolved in ethyl acetate (250 mL)
  4. dry with materialdried (MgSO4)
  5. customThe product crystallized upon concentration of the ethyl acetate

出典と根拠

ORDレコード
ord-9d83eef5c4f341579589f6ef34e28cdc
出典データセット
uspto-grants-2014_12
特許番号
US08916566B2

反応ノート

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