Hydrochloric Acid → 7-Fluoro-1-methyl-5-nitro-1,3-dihydro-indol-2-one

HRID 2114869노트

반응식

HRID 2114869 반응식
F[C:2]1[C:7]([F:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[CH2:12][C:13]([OH:15])=O.[CH3:16][NH2:17].O.Cl>CS(C)=O>[F:8][C:7]1[CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[CH:4]=[C:3]2[C:2]=1[N:17]([CH3:16])[C:13](=[O:15])[CH2:12]2

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 6329MethylamineHCID 11951676(2,3-Difluoro-5-nitrophenyl)acetic acid

생성물 1

HCID 119516757-Fluoro-1-methyl-5-nitro-1,3-dihydro-indol-2-one

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
45 °C

실험 절차

Crude (2,3-difluoro-5-nitrophenyl)acetic acid (12, 1.00 g, 0.00461 mol) and a 40% solution of methylamine in water (3 eq., 1.20 ml, 0.0138 mol) are mixed in DMSO (5 ml) and stirred at 45° C. for 1 hour. 2N Hydrochloric acid (20 ml) is added in one portion and the mixture stirred at room temperature for 1 hour. The reaction mixture is extracted with ethyl acetate and the extract washed with saturated aqueous sodium bicarbonate and brine, dried (MgSO4) and evaporated. The residue is purified by flash column chromatography (50% ethyl acetate/hexane) to give the title compound as a solid. HPLC r.t. 4.4 min.

후처리

  1. stirringthe mixture stirred at room temperature for 1 hour
  2. extractionThe reaction mixture is extracted with ethyl acetate
  3. washthe extract washed with saturated aqueous sodium bicarbonate and brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue is purified by flash column chromatography (50% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-b457b77ac1fc43cfaa66861c5d21f889
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07435751B2

반응 노트

불러오는 중…