Sodium Hydroxide → 3-methoxy-4-nitro-N-[2-(5-carboxypent-1-yloxy)-4-methylphenyl]-N-methylbenzamide

HRID 1005579Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1005579
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:28]=[CH:29][C:30]=1[N+:31]([O-:33])=[O:32])[C:6]([N:8]([C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:11]=1[O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25]CC)=[O:24])[CH3:9])=[O:7].[OH-].[Na+]>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:28]=[CH:29][C:30]=1[N+:31]([O-:33])=[O:32])[C:6]([N:8]([C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:11]=1[O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])[CH3:9])=[O:7]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 220107713-methoxy-4-nitro-N-[2-(5-ethoxycarbonylpent-1-yloxy)-4-methylphenyl]-N-methylbenzamide

Produkt 1

HCID 187914763-methoxy-4-nitro-N-[2-(5-carboxypent-1-yloxy)-4-methylphenyl]-N-methylbenzamideAusbeute 99,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 3-methoxy-4-nitro-N-[2-(5-ethoxycarbonylpent-1-yloxy)-4-methylphenyl]-N-methylbenzamide (7.6 g) in ethanol (76 ml) was treated with 1 N sodium hydroxide solution (33 ml) at ambient temperature and the mixture was stirred at the same temperature for 6 hours. The reaction was quenched by the dropwise addition of 1 N hydrochloric acid (35 ml). The mixture was concentrated and the residue was dissolved in a mixture of ethyl acetate and 1 N hydrochloric acid. The extracted organic layer was washed with brine and dried over magnesium sulfate. The suspension was filtered and the solvent was removed by evaporation to give 3-methoxy-4-nitro-N-[2-(5-carboxypent-1-yloxy)-4-methylphenyl]-N-methylbenzamide (7.1 g) as an oil.

Aufarbeitung

  1. customThe reaction was quenched by the dropwise addition of 1 N hydrochloric acid (35 ml)
  2. concentrationThe mixture was concentrated
  3. dissolutionthe residue was dissolved in a mixture of ethyl acetate and 1 N hydrochloric acid
  4. washThe extracted organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationThe suspension was filtered
  7. customthe solvent was removed by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-5987305824104f4c97bc0c8503d80798
Quelldatensatz
uspto-grants-2000_04
Patentnummer
US06054457

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