Potassium Carbonate → 3-Fluoro-4-nitroaniline

HRID 468510

反応式

HRID 468510 の反応式
[F:1][C:2]1[CH:3]=[C:4]([NH:11]C(=O)C(C)(C)C)[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl.Cl.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9])[NH2:11]

参加物

6

反応物 2

HCID 11430Potassium CarbonateHCID 59129487N-(3-fluoro-4-nitro-phenyl)-2,2-dimethyl-propionamide

生成物 1

HCID 754013-Fluoro-4-nitroaniline収率 99.6%

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid溶媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of N-(3-fluoro-4-nitro-phenyl)-2,2-dimethyl-propionamide (87.0 g, 0.36 mol) in CH2Cl2 (400 mL) and 6N hydrochloric acid (800 mL) was heated to reflux for 2 hours. The reaction mixture was cooled to room temperature. The reaction mixture was diluted with 1000 mL of ethyl acetate and potassium carbonate (500.0 g) was added portion wise. The aqueous solution was separated and the organic layer was washed with brine and dried over anhydrous Na2SO4. The solvent was removed by evaporation under reduced pressure; the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 30:1) to afford 3-fluoro-4-nitroaniline (56.0 g, 99%). 1H NMR (300 MHz, CDCl3) δ 8.07 (t, J=8.7 Hz, 1H), 7.86 (dd, J=2.1, 13.2 Hz 1H), 7.59 (brs, 2H), 7.22 (s, 1H).

後処理

  1. temperaturewas heated
  2. temperatureto reflux for 2 hours
  3. additionwas added portion wise
  4. customThe aqueous solution was separated
  5. washthe organic layer was washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. customThe solvent was removed by evaporation under reduced pressure
  8. customthe residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 30:1)

出典と根拠

ORDレコード
ord-3631f362aea14a94ad2647fd82f0fdab
出典データセット
uspto-grants-2014_01
特許番号
US08623905B2

関連ノート

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