Triethylamine → Methyl 5-chloro-2-methoxynicotinate

HRID 1388518Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1388518
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]([OH:12])=[O:11])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[CH2:13](N(CC)CC)C>CO>[Cl:1][C:2]1[CH:3]=[C:4]([C:10]([O:12][CH3:13])=[O:11])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 8471TriethylamineHCID 98369735-Chloro-2-methoxynicotinic acid

Produkt 1

HCID 13282891Methyl 5-chloro-2-methoxynicotinate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

By the procedure of Example 1, 5-chloro-2-methoxypyridine-3-carboxylic acid [Sarges et al., J. Med. Chem. 19, 709 (1976); 10 g.]was converted to its acid chloride, which was added in one portion to 150 ml. of methanol (slight exotherm), then made basic with triethylamine (approximately 1.1 equivalents). The reaction mixture was evaporated to solids and the residue partitioned between ethyl acetate and water. The ethyl acetate layer was washed with fresh water and then brine, dried over anhydrous magnesium sulfate, filtered and evaporated to yield title product [9.75 g., m.p. 79°-81° C.; pnmr/CDCl3 /delta (ppm) 3.8 (s, 3H), 4.1 (s, 3H), 8.1 (d, 1H), 8.3 (d, 1H)].

Aufarbeitung

  1. additionwas added in one portion to 150 ml
  2. customThe reaction mixture was evaporated to solids
  3. customthe residue partitioned between ethyl acetate and water
  4. washThe ethyl acetate layer was washed with fresh water
  5. dry with materialbrine, dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-5463804fa8554ee2a72ef16d945d0994
Quelldatensatz
uspto-grants-1984_02
Patentnummer
US04431810

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