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4-cyano-2,5-difluoro-N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-3-nitro-benzamide → 3-amino-4-cyano-2,5-difluoro-N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-benzamide

HRID 1943121
ノート
印刷プレビュー

反応式

HRID 1943121 の反応式
[C:1]([C:3]1[C:29]([F:30])=[CH:28][C:6]([C:7]([NH:9][C:10]2[C:15]([CH3:16])=[CH:14][C:13]([C:17]([F:26])([C:22]([F:25])([F:24])[F:23])[C:18]([F:21])([F:20])[F:19])=[CH:12][C:11]=2[CH3:27])=[O:8])=[C:5]([F:31])[C:4]=1[N+:32]([O-])=O)#[N:2].[H][H]>CO.[Pd]>[NH2:32][C:4]1[C:5]([F:31])=[C:6]([CH:28]=[C:29]([F:30])[C:3]=1[C:1]#[N:2])[C:7]([NH:9][C:10]1[C:15]([CH3:16])=[CH:14][C:13]([C:17]([F:26])([C:18]([F:19])([F:20])[F:21])[C:22]([F:24])([F:25])[F:23])=[CH:12][C:11]=1[CH3:27])=[O:8]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 592269494-cyano-2,5-difluoro-N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-3-nitro-benzamideHCID 178418361HCID 178418361、化合物

生成物 1

HCID 592269483-amino-4-cyano-2,5-difluoro-N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-benzamide収率 17%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒
HCID 887
Methanol
溶媒

実験手順

A solution of 4-cyano-2,5-difluoro-N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-3-nitro-benzamide (5.99 g, 12 mmol) (Example I16) in methanol was reacted with hydrogen for 16 hours in the presence of 10% palladium on carbon (40 bar, 40° C.). The reaction mixture was filtered to remove the catalyst and the filtrate concentrated. The residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 7:3) to give 3-amino-4-cyano-2,5-difluoro-N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-benzamide (0.953 g, 17% yield). 1H-NMR (400 MHz, CDCl3): 2.36 (6H, s), 4.82 (2H, bs), 7.12 (1H, m), 7.38 (2H, s), 7.78 (1H, d) ppm.

後処理

  1. filtrationThe reaction mixture was filtered
  2. customto remove the catalyst
  3. concentrationthe filtrate concentrated
  4. customThe residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 7:3)

出典と根拠

ORDレコード
ord-3ab6cc9383074d4281eb6adf51195d0f
出典データセット
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08389766B2

反応ノート

読み込み中…

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