Hydrogen Bromide → 2-Bromo-6-hydroxymethyl-3-[8(4-methoxyphenyl)octyloxy]pyridine hydrobromide

HRID 264784

Reaktionsgleichung

Reaktionsgleichung von HRID 264784
[Br:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([CH2:9][OH:10])[N:3]=1.ClC[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+].Br>CN(C)C=O.C(O)CCC.O>[BrH:1].[Br:1][C:2]1[C:7]([O:8][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]2[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=2)=[CH:6][CH:5]=[C:4]([CH2:9][OH:10])[N:3]=1

Komponenten

8

Edukt 4

HCID 260Hydrogen BromideHCID 11430Potassium Carbonate2×HCID 160446662-Bromo-6-(hydroxymethyl)pyridin-3-ol2×HCID 572241481-Chloro-8-(4-anisyl)-octane

Produkt 1

HCID 196927152-Bromo-6-hydroxymethyl-3-[8(4-methoxyphenyl)octyloxy]pyridine hydrobromide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 2631-ButanolLösungsmittelHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

The crude 2-bromo-3-hydroxy-6-hydroxymethylpyridine (vide supra, 1.12 mol) was dissolved in dimethyl formamide (1150 ml) at 60° C. 1-Chloro-8-(4-anisyl)-octane (342 g, 1.34 mmol) and potassium carbonate (388 g, 2.81 mol) were added. It was found to be important that the potassium carbonate was ground to as fine a powder as possible. The mixture was stirred vigorously and heated to 90°-95° C. until the assay of 2-bromo-3-hydroxy-6-hydroxymethylpyridine (by HPLC) fell below 3% (approx 5 h). The mixture was then cooled to room temperature, poured into water (10 L) and extracted with ethyl acetate (3×670 ml). The combined ethyl acetate extracts were washed with water (2×500 ml) and dried before being evaporated to dryness. The crude reaction product was dissolved in butan-1-ol (2700 ml) and hydrogen bromide gas (120 g) passed through the solution keeping the temperature below 70° C. After allowing the mixture to cool to 10° C. with vigorous stirring the solid product was filtered and washed with ethyl acetate (2×500 ml). The solid product was dried under vacuum at 60° C. for 4 days. Yield 421 g, 75%.

Aufarbeitung

  1. custombelow 3% (approx 5 h)
  2. extractionextracted with ethyl acetate (3×670 ml)
  3. washThe combined ethyl acetate extracts were washed with water (2×500 ml)
  4. customdried
  5. custombefore being evaporated to dryness
  6. customThe crude reaction product
  7. customthe temperature below 70° C
  8. temperatureto cool to 10° C.
  9. stirringwith vigorous stirring the solid product
  10. filtrationwas filtered
  11. washwashed with ethyl acetate (2×500 ml)
  12. customThe solid product was dried under vacuum at 60° C. for 4 days

Quellen und Nachweise

ORD-Eintrag
ord-a657f60c1c0c45fdb0e9aeb0b46f5041
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05646286

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