4-Methylmorpholine → 3-Bromo-4-(pyrrolidin-1-ylcarbonyl)benzoic acid

HRID 2053761Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2053761
[Br:1][C:2]1[CH:10]=[C:9]([C:11]([OH:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1.CN1CCOCC1>CN(C)C=O>[Br:1][C:2]1[CH:10]=[C:9]([CH:8]=[CH:7][C:3]=1[C:4]([N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:6])[C:11]([OH:13])=[O:12]

Komponenten

5

Edukt 3

HCID 79724-MethylmorpholineHCID 31268PyrrolidineHCID 68513Bromoterephthalic acid

Produkt 1

HCID 693124883-Bromo-4-(pyrrolidin-1-ylcarbonyl)benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

100 g (0.388 mol) of 2-bromoterephthalic acid is dissolved in 700 mL of N,N-dimethylformamide and slowly combined with 69.2 g (0.427 mol) of N,N′-carbonyldiimidazole with stirring. After total dissolution, the mixture is stirred for 15 minutes at ambient temperature and then 48.5 mL (0.582 mol) of pyrrolidine and 93.9 mL (0.854 mol) of N-methylmorpholine are slowly added dropwise one after the other. The mixture is stirred for 2.5 days at ambient temperature and then concentrated in vacuo. The residue is combined with distilled water and acidified with 2 molar hydrochloric acid solution. The aqueous phase is extracted with ethyl acetate. The precipitate formed is suction filtered and dried at 40° C. Yield: 29.4 g (25%); Rf value: 0.30 (silica gel; dichloromethane/ethanol=9:1); C12H12BrNO3 (298.14); mass spectrum: (M+H)+=298/300 (bromine isotope).

Aufarbeitung

  1. dissolutionAfter total dissolution
  2. stirringthe mixture is stirred for 15 minutes at ambient temperature
  3. stirringThe mixture is stirred for 2.5 days at ambient temperature
  4. concentrationconcentrated in vacuo
  5. extractionThe aqueous phase is extracted with ethyl acetate
  6. customThe precipitate formed
  7. filtrationfiltered
  8. customdried at 40° C

Quellen und Nachweise

ORD-Eintrag
ord-e516b1851eda4a3ab51ad14884abd9a5
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07326791B2

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