Ethyl-[2-amino-3-nitro-6-(trifluoromethyl)-pyridin-4-yl]-benzylcarbamate → Ethyl-[2,3-diamino-6-(trifluoromethyl)-pyridin-4-yl]-benzylcarbamate

HRID 386420

反応式

HRID 386420 の反応式
[CH2:1]([O:3][C:4](=[O:27])[N:5]([C:13]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[N:16]=[C:15]([NH2:23])[C:14]=1[N+:24]([O-])=O)[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2]>C(O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:27])[N:5]([C:13]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[N:16]=[C:15]([NH2:23])[C:14]=1[NH2:24])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2]

参加物

4

反応物 1

HCID 67454545Ethyl-[2-amino-3-nitro-6-(trifluoromethyl)-pyridin-4-yl]-benzylcarbamate

生成物 1

HCID 54753661Ethyl-[2,3-diamino-6-(trifluoromethyl)-pyridin-4-yl]-benzylcarbamate収率 60%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

Crude ethyl-[2-amino-3-nitro-6-(trifluoromethyl)-pyridin-4-yl]-benzylcarbamate (65 gm, 170 mmol) was dissolved in ethanol (1000 mL) and 10% Pd—C (6 g m) was added. Hydrogenation at 40° C. and 40 psi for 1 hour gave complete reduction of the nitro group. The catalyst was removed by filtration and the filtrate evaporated to dryness under reduced pressure to give a light brown semi-solid. Trituration with t-butyl methyl ether (150 mL) followed by filtration and washing with the same solvent (30 mL) gave ethyl-[2,3-diamino-6-(trifluoromethyl)-pyridin-4-yl]-benzylcarbamate (36 gm, 60% yield) as a white solid.

後処理

  1. customHydrogenation at 40° C. and 40 psi for 1 hour gave complete reduction of the nitro group
  2. customThe catalyst was removed by filtration
  3. customthe filtrate evaporated to dryness under reduced pressure
  4. customto give a light brown semi-solid
  5. filtrationTrituration with t-butyl methyl ether (150 mL) followed by filtration
  6. washwashing with the same solvent (30 mL)

出典と根拠

ORDレコード
ord-aaa0b11755e9478585cbe5edef2928df
出典データセット
uspto-grants-2013_02
特許番号
US08372836B2

関連ノート

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