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

HRID 705087노트

반응식

HRID 705087 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-373345b756414a578cad9f76f13cf374
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09173861B2

반응 노트

불러오는 중…