Pyridine → 4-acetoxy-N-(2-methyl-5-nitrophenyl)benzamide

HRID 1369498

Reaktionsgleichung

Reaktionsgleichung von HRID 1369498
C(Cl)(=O)C(Cl)=O.[C:7]([O:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=1)(=[O:9])[CH3:8].[CH3:20][C:21]1[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][C:22]=1[NH2:23].N1C=CC=CC=1>CN(C=O)C.C(Cl)Cl>[CH3:20][C:21]1[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][C:22]=1[NH:23][C:15](=[O:17])[C:14]1[CH:13]=[CH:12][C:11]([O:10][C:7](=[O:9])[CH3:8])=[CH:19][CH:18]=1

Komponenten

7

Edukt 4

HCID 1049PyridineHCID 74442-Methyl-5-NitroanilineHCID 16865Benzoic acid, 4-(acetyloxy)-HCID 65578Oxalyl chloride

Produkt 1

HCID 7763404-acetoxy-N-(2-methyl-5-nitrophenyl)benzamideAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Oxalyl chloride (0.5 ml) was added slowly to a stirred mixture of 4-acetoxybenzoic acid (1.09 g), methylene chloride (30 ml) and DMF (one drop) and the mixture was stirred at ambient temperature for 2 hours. A solution of 2-methyl-5-nitroaniline (0.76 g) and pyridine (2 ml) in methylene chloride was added over 15 minutes and the mixture was stirred for a further 2 hours. The reaction mixture washed with a 5% aqueous acetic acid solution, with water and with a 5% aqueous sodium bicarbonate solution. The organic extract was dried (MgSO4) and evaporated. The residue was recrystallised from ethyl acetate to give N-(2-methyl-5-nitrophenyl)-4-acetoxybenzamide (0.8 g), m.p. 207-208° C.; NMR Spectrum: (DMSOd6) 2.3 (s, 3H), 7.31 (d, 2H), 7.56 (d, 1H), 8.02 (m, 3H), 8.47 (d, 1H), 10.12 (s, 1H).

Aufarbeitung

  1. stirringthe mixture was stirred for a further 2 hours
  2. washThe reaction mixture washed with a 5% aqueous acetic acid solution, with water and with a 5% aqueous sodium bicarbonate solution
  3. extractionThe organic extract
  4. dry with materialwas dried (MgSO4)
  5. customevaporated
  6. customThe residue was recrystallised from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-068f2cac75754dfdbcfed7229969aa26
Quelldatensatz
uspto-grants-2003_06
Patentnummer
US06579872B1

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