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

HRID 2114869ノート

反応式

HRID 2114869 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
45 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-b457b77ac1fc43cfaa66861c5d21f889
出典データセット
uspto-grants-2008_10
特許番号
US07435751B2

反応ノート

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