Ammonium Chloride → 5-Amino4-(3-aminobenzoyl)-1-(4-fluorophenyl)pyrazole

HRID 843078ノート

反応式

HRID 843078 の反応式
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[C:14](=[O:24])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-])=O)[CH:16]=1.[Cl-].[NH4+]>C(O)C.O.[Fe]>[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[C:14](=[O:24])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([NH2:21])[CH:16]=1

参加物

6

反応物 2

HCID 25517Ammonium ChlorideHCID 222627595-Amino-1-(4-fluorophenyl)-4-(3-nitrobenzoyl)pyrazole

生成物 1

HCID 222628105-Amino4-(3-aminobenzoyl)-1-(4-fluorophenyl)pyrazole収率 96.4%

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

A mixture of 5-amino-1-(4-fluorophenyl)-4-(3-nitrobenzoyl)pyrazole (4.0 g, 24.52), Fe powder (3.84 g, 68 mmol) and ammonium chloride (3.84, 71.78 mmol) in ethanol (135 ml) and water (64 ml) was heated at reflux under nitrogen atmosphere. After 1 h, the reaction mixture was cooled to room temperature and stirred overnight. The reaction mixture was filtered through Celite® and the filtrate was concentrated in vacuo. The residue was partitioned between water and ethyl acetate. The organic layer was separated and washed with brine, dried over sodium sulfate and concentrated in vacuo to give 5-amino-4-(3-aminobenzoyl)-1-(4-fluorophenyl)pyrazole (3.5 g) as a solid.

後処理

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen atmosphere
  3. filtrationThe reaction mixture was filtered through Celite®
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was partitioned between water and ethyl acetate
  6. customThe organic layer was separated
  7. washwashed with brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-77288735c45640be8390861ee3e9e8b3
出典データセット
uspto-grants-2002_04
特許番号
US06376527B1

反応ノート

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