Stannous Chloride → 5-Amino-4'-methyl-biphenyl-3-carboxylic acid (2-methoxy-1-methyl-ethyl)-amide

HRID 705087ノート

反応式

HRID 705087 の反応式
[CH3:1][O:2][CH2:3][CH:4]([NH:6][C:7]([C:9]1[CH:10]=[C:11]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)[CH:12]=[C:13]([N+:15]([O-])=O)[CH:14]=1)=[O:8])[CH3:5].Cl[Sn]Cl>CO>[CH3:1][O:2][CH2:3][CH:4]([NH:6][C:7]([C:9]1[CH:10]=[C:11]([C:18]2[CH:19]=[CH:20][C:21]([CH3:24])=[CH:22][CH:23]=2)[CH:12]=[C:13]([NH2:15])[CH:14]=1)=[O:8])[CH3:5]

参加物

4

反応物 2

HCID 24479Stannous ChlorideHCID 595997024'-Methyl-5-nitro-biphenyl-3-carboxylic acid (2-methoxy-1-methyl-ethyl)-amide

生成物 1

HCID 595997035-Amino-4'-methyl-biphenyl-3-carboxylic acid (2-methoxy-1-methyl-ethyl)-amide収率 90.3%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a stirred solution of 4′-methyl-5-nitro-biphenyl-3-carboxylic acid (2-methoxy-1-methyl-ethyl)-amide (39 mmol) in 250 ml methanol was added SnCl2 (117 mmol) in one portion at room temperature. The reaction mixture was heated to reflux for 3 hours. Solvent was removed under reduced pressure and the residue was diluted with ethyl acetate and treated with saturated NaHCO3 solution. Solids were filtered off and the filtrate was washed with saturated aqueous NaHCO3, brine, dried over anhydrous Na2SO4, filtered and concentrated in vaccuo to give 5-amino-4′-methyl-biphenyl-3-carboxylic acid (2-methoxy-1-methyl-ethyl)-amide as a yellow oil (10.5g, 90.3%). MS (M+H)=299.

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 3 hours
  3. customSolvent was removed under reduced pressure
  4. additionthe residue was diluted with ethyl acetate
  5. additiontreated with saturated NaHCO3 solution
  6. filtrationSolids were filtered off
  7. washthe filtrate was washed with saturated aqueous NaHCO3, brine
  8. dry with materialdried over anhydrous Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vaccuo

出典と根拠

ORDレコード
ord-373345b756414a578cad9f76f13cf374
出典データセット
uspto-grants-2015_11
特許番号
US09173861B2

反応ノート

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