Hydrochloric Acid → HCID 13564462, Verbindung

HRID 1284557Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1284557
[OH:1][C:2]1[C:11]([CH:12]=O)=[C:6]2[CH2:7][CH2:8][CH2:9][O:10][C:5]2=[CH:4][CH:3]=1.[F:14][C:15]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:16]=1[NH2:17].[BH4-].[Na+].Cl>CO.O>[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][CH2:8][CH2:7][C:6]=2[C:11]=1[CH2:12][NH:17][C:16]1[CH:18]=[CH:19][C:20]([F:22])=[CH:21][C:15]=1[F:14]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 97092,4-DifluoroanilineHCID 4311764Sodium borohydrideHCID 13564460HCID 13564460, Verbindung

Produkt 1

HCID 13564462HCID 13564462, VerbindungAusbeute 96,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 6-hydroxy-3,4-dihydrobenzopyran-5-carboxaldehyde (299 mg, 1.68 mmol) and 2,4 -difluoroaniline (219 mg, 1.68 mmol) in methanol (8 mL) was heated to reflux for 20 minutes during which time the intermediate Schiff's base crystallized, and, after cooling to room temperature, was collected by filtration and dried. The isolated Schiff's base (175 mg, 36%) was suspended in methanol (8 mL) and sodium borohydride (25 mg, 0.66 mmol) was added. The mixture was stirred at room temperature for 5 minutes, poured into water (50 mL) and carefully neutralized (pH=7) with 2.5 N HCl. The product was collected by filtration and dried to afford 6-hydroxy-5-(2,4-difluorophenyl)aminomethyl-3, 4-dihydrobenzopyran, (170 mg, 96.6%), m.p. 120°-121° C.

Aufarbeitung

  1. temperaturewas heated
  2. customcrystallized
  3. filtrationwas collected by filtration
  4. customdried
  5. filtrationThe product was collected by filtration
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-a1974683faef44ccb8e4dad523e0aac3
Quelldatensatz
uspto-grants-1986_01
Patentnummer
US04563476

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