Hydrochloric Acid → Dimethyl 2,5-bis{(4-methoxyphenyl)amino}cyclohexa-1,4-diene-1,4-dicarboxylate

HRID 2056974

Reaktionsgleichung

Reaktionsgleichung von HRID 2056974
[CH3:1][O:2][C:3]([CH:5]1[C:11](=O)[CH2:10][CH:9]([C:13]([O:15][CH3:16])=[O:14])[C:7](=O)[CH2:6]1)=[O:4].[CH3:17][O:18][C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1.Cl>CO>[CH3:17][O:18][C:19]1[CH:25]=[CH:24][C:22]([NH:23][C:7]2[CH2:6][C:5]([C:3]([O:2][CH3:1])=[O:4])=[C:11]([NH:23][C:22]3[CH:24]=[CH:25][C:19]([O:18][CH3:17])=[CH:20][CH:21]=3)[CH2:10][C:9]=2[C:13]([O:15][CH3:16])=[O:14])=[CH:21][CH:20]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 7732P-AnisidineHCID 948661,4-Cyclohexanedicarboxylic acid, 2,5-dioxo-, 1,4-dimethyl ester

Produkt 1

HCID 14745936Dimethyl 2,5-bis{(4-methoxyphenyl)amino}cyclohexa-1,4-diene-1,4-dicarboxylateAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Dimethyl 1,4-cyclohexanedione-2,5-dicarboxylate (9.12 gm; 40 mmol) and methanol (200 ml) were heated to boiling, then 4-methoxyaniline (10.84 gm; 88 mmol) was added followed by conc. hydrochloric acid (400 μl). The mixture was refluxed for 2.5 hours under a nitrogen atmosphere. On cooling, an orange solid precipitated out which was collected by filtration, washed with methanol and dried under vacuum to give 17.0 gm (97%) of dimethyl 2,5-bis{(4-methoxyphenyl)amino}cyclohexa-1,4-diene-1,4-dicarboxylate.

Aufarbeitung

  1. temperatureThe mixture was refluxed for 2.5 hours under a nitrogen atmosphere
  2. temperatureOn cooling
  3. customan orange solid precipitated out which
  4. filtrationwas collected by filtration
  5. washwashed with methanol
  6. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-30b319bbc6594d7aaf1c7b3c319f8fdd
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07335771B2

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