Hydrochloric Acid → 1-(2-Chloro-4-fluoro-5-methylcarbonylaminophenyl)ethyl nitrate

HRID 231415ノート

反応式

HRID 231415 の反応式
[N+:1]([O-:17])([O:3][CH:4]([C:6]1[CH:11]=[C:10]([N+:12]([O-])=O)[C:9]([F:15])=[CH:8][C:7]=1[Cl:16])[CH3:5])=[O:2].[C:18](OC(=O)C)(=[O:20])[CH3:19].[H][H].Cl>[Pt]=O.O.C(OCC)(=O)C>[N+:1]([O-:17])([O:3][CH:4]([C:6]1[CH:11]=[C:10]([NH:12][C:18]([CH3:19])=[O:20])[C:9]([F:15])=[CH:8][C:7]=1[Cl:16])[CH3:5])=[O:2]

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 14501806HCID 14501806、化合物HCID 178418361HCID 178418361、化合物

生成物 1

HCID 145018071-(2-Chloro-4-fluoro-5-methylcarbonylaminophenyl)ethyl nitrate

試薬・触媒・溶媒 3

HCID 82844Platinum oxide (PtO)触媒HCID 962Water溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

In a Parr hydrogenation apparatus were placed 3.7 g (0.014 mole) of 1-(2-chloro-4-fluoro-5-nitrophenyl)ethyl nitrate, 0.35 g of platinum oxide catalyst, 35 ml of ethyl acetate, and 10 ml of acetic anhydride. The apparatus was pressurized with hydrogen, and the reaction was allowed to continue until the pressure ceased dropping. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure leaving a residue. This residue was mixed with 15 ml of water and 5 ml of 10% hydrochloric acid. This mixture was stirred at room temperature for two hours. Following dilution with water, the mixture was extracted with methylene chloride. The extracts were combined and washed successively with water, 5% hydrochloric acid, and a saturated, aqueous solution of sodium bicarbonate. This solution was dried, filtered, and the solvent was evaporated under reduced pressure leaving a residue. This residue was passed through a column of silica gel, eluting first with ethyl acetate/heptane (1/4) and then with ethyl acetate/heptane (1/1). The appropriate fractions were collected, and the solvent was evaporated under reduced pressure yielding 1.7 g of 1-(2-chloro-4-fluoro-5-methylcarbonylaminophenyl)ethyl nitrate as a white solid. The nmr and ir spectra were consistent with the proposed structure.

後処理

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customleaving a residue
  4. extractionthe mixture was extracted with methylene chloride
  5. washwashed successively with water, 5% hydrochloric acid
  6. customThis solution was dried
  7. filtrationfiltered
  8. customthe solvent was evaporated under reduced pressure
  9. customleaving a residue
  10. washeluting first with ethyl acetate/heptane (1/4)
  11. customThe appropriate fractions were collected
  12. customthe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-e963942e100b41f8b8c668601e82eeea
出典データセット
uspto-grants-1989_07
特許番号
US04846875

反応ノート

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