Hydrochloric Acid → N-[4-(hydroxymethyl)phenyl]-4-methoxy-N-methylbenzamide

HRID 1242894

Reaktionsgleichung

Reaktionsgleichung von HRID 1242894
C1COCC1.B.[CH3:7][O:8][C:9]1[CH:27]=[CH:26][C:12]([C:13]([N:15]([C:17]2[CH:25]=[CH:24][C:20]([C:21](O)=[O:22])=[CH:19][CH:18]=2)[CH3:16])=[O:14])=[CH:11][CH:10]=1.Cl>O>[OH:22][CH2:21][C:20]1[CH:19]=[CH:18][C:17]([N:15]([CH3:16])[C:13](=[O:14])[C:12]2[CH:26]=[CH:27][C:9]([O:8][CH3:7])=[CH:10][CH:11]=2)=[CH:25][CH:24]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 8028Tetrahydrofuran2×HCID 219397344-[N-(4-Methoxybenzoyl)-N-methylamino]benzoic acid

Produkt 1

HCID 21939995N-[4-(hydroxymethyl)phenyl]-4-methoxy-N-methylbenzamideAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

THF solution (1M, 16 ml) of borane was added dropwise to THF solution (10 ml) of 4-[N-(4-methoxybenzoyl)-N-methylamino]benzoic acid (1.14 g) under ice-cooling, which was stirred for 15 minutes, and then stirred at room temperature for 1 hour. After water was added to the reaction mixture, 1N hydrochloric acid was further added, and extraction was conducted using ethyl acetate. The organic layer was washed with water and saturated sodium bicarbonate, and saturated aqueous sodium chloride solution, dried, and then concentrated. The residue was purified using silica gel chromatography (development solvent; hexane˜hexane:ethyl acetate=1:2), and recrystallized (ethyl acetate-hexane) to give the titled compound (770 mg).

Aufarbeitung

  1. temperaturecooling
  2. stirringstirred at room temperature for 1 hour
  3. additionwas further added
  4. extractionextraction
  5. washThe organic layer was washed with water and saturated sodium bicarbonate, and saturated aqueous sodium chloride solution
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified
  9. customrecrystallized (ethyl acetate-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-dbdbb6ccd20c407f9823262629c5779a
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07115750B1

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