N-(4-Methyl-3-nitrophenyl)-3-(trifluoromethyl)benzamide → N-(3-amino-4-methylphenyl)-3-(trifluoromethyl)benzamide

HRID 1038661

反応式

HRID 1038661 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:20])[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)=[CH:4][C:3]=1[N+:21]([O-])=O>[Pd].C(O)C>[NH2:21][C:3]1[CH:4]=[C:5]([NH:8][C:9](=[O:20])[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:17])([F:18])[F:19])[CH:11]=2)[CH:6]=[CH:7][C:2]=1[CH3:1]

参加物

4

反応物 1

HCID 11716802N-(4-Methyl-3-nitrophenyl)-3-(trifluoromethyl)benzamide

生成物 1

HCID 11529455N-(3-amino-4-methylphenyl)-3-(trifluoromethyl)benzamide

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

A suspension of N-(4-methyl-3-nitro-phenyl)-3-trifluoromethyl-benzamide (9.91 g, 30.6 mmol) and 10% palladium on charcoal (990 mg) in ethanol (180 ml) is hydrogenated at atmospheric pressure and room temperature. After 2 h the reaction is complete, the catalyst is removed by filtration through Celite, and the filtrate is evaporated to dryness. Recrystallization of the crude product from ethyl acetate/hexanes followed by vacuum drying at 45° C. overnight affords the title compound as fluffy light grey needles: HPLC: tR=5.38 min (purity: >99%, gradient A), ESI-MS: 295.3 [MH]+

後処理

  1. customis hydrogenated at atmospheric pressure and room temperature
  2. customthe catalyst is removed by filtration through Celite
  3. customthe filtrate is evaporated to dryness
  4. customRecrystallization of the crude product from ethyl acetate/hexanes
  5. customdrying at 45° C. overnight

出典と根拠

ORDレコード
ord-ad0394b2d54c4b50925131c22bea3b2f
出典データセット
uspto-grants-2013_10
特許番号
US08552002B2

関連ノート

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