P-Anisidine → 3-Hydroxy-4'-methoxy-2-nitrobenzanilide

HRID 478167

Reaktionsgleichung

Reaktionsgleichung von HRID 478167
[OH:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.[CH3:14][O:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>CN(C)C=O.C(N(CC)CC)C>[OH:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH:20][C:19]1[CH:21]=[CH:22][C:16]([O:15][CH3:14])=[CH:17][CH:18]=1)=[O:7]

Komponenten

7

Edukt 4

HCID 7732P-AnisidineHCID 757711-HydroxybenzotriazoleHCID 2932913-Hydroxy-2-nitrobenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Produkt 1

HCID 180011313-Hydroxy-4'-methoxy-2-nitrobenzanilideAusbeute 70,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

3-Hydroxy-2-nitrobenzoic acid (1.83 g) was dissolved in 50 ml of N,N-dimethylformamide, then 1.23 g of 4-methoxyaniline, 2.50 g of 1-ethyl-3-dimethylaminopropylcarbodiimide hydrochloride, 1.35 g of 1-hydroxybenzotriazole and 1.81 ml of triethylamine were added and the mixture was stirred at room temperature for 66 hours. The reaction solution was concentrated in vacuo, water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated in vacuo. Chloroform was added to the resulting residue and the resulting precipitate was filtered to give 2.04 g of 3-hydroxy-4′-methoxy-2-nitrobenzanilide. The filtrate was purified by silica gel column chromatography using chloroform-methanol (98:2) as an eluting solvent, chloroform was added to the resulting crude product and the resulting precipitate was filtered to give additional 0.24 g of 3-hydroxy-4′-methoxy-2-nitrobenzanilide.

Aufarbeitung

  1. concentrationThe reaction solution was concentrated in vacuo, water
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. additionChloroform was added to the resulting residue
  8. filtrationthe resulting precipitate was filtered

Quellen und Nachweise

ORD-Eintrag
ord-b9d5b51038774f9197b1e5a828a4cd10
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06642224B1

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