Water → Methyl 2-amino-5-bromonicotinate

HRID 646724

Reaktionsgleichung

Reaktionsgleichung von HRID 646724
[NH2:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][C:5]([Br:11])=[CH:4][N:3]=1.OS(O)(=O)=O.O.[C:18](=O)([O-])[O-].[Na+].[Na+]>CO.C(OCC)(=O)C>[NH2:1][C:2]1[C:7]([C:8]([O:10][CH3:18])=[O:9])=[CH:6][C:5]([Br:11])=[CH:4][N:3]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 7374452-Amino-5-bromonicotinic acid

Produkt 1

HCID 2763453Methyl 2-amino-5-bromonicotinateAusbeute 73,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A slurry of 2-amino-5-bromopyridine-3-carboxylic acid (7 g, 32.2 mmol) in methanol (150 mL) and H2SO4 (7 mmol) was heated to reflux for 48 h. The reaction mixture was concentrated to ca. 40 mL. Water (100 mmol) was added to the residual oil, and the mixture neutralized with sodium carbonate. Ethyl acetate (400 mL) was added and the organic layer was washed with saturated aqueous sodium chloride then dried (Na2SO4) and concentrated to give the title compound (5.5 g, 73.9% yield).

Aufarbeitung

  1. temperatureto reflux for 48 h
  2. concentrationThe reaction mixture was concentrated to ca. 40 mL
  3. washthe organic layer was washed with saturated aqueous sodium chloride
  4. dry with materialthen dried (Na2SO4)
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-43ab49ea88d541d0b6298495788b4593
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07704995B2

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