Benzyl Bromide → 5-[(Benzyloxy)carbonyl]nicotinic acid

HRID 2250617

Reaktionsgleichung

Reaktionsgleichung von HRID 2250617
[H-].[Na+].[N:3]1[CH:8]=[C:7]([C:9]([OH:11])=[O:10])[CH:6]=[C:5]([C:12]([OH:14])=[O:13])[CH:4]=1.Br[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C)C=O>[CH2:16]([O:10][C:9]([C:7]1[CH:8]=[N:3][CH:4]=[C:5]([CH:6]=1)[C:12]([OH:14])=[O:13])=[O:11])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 103663,5-Pyridinedicarboxylic acidHCID 24758Sodium hydride

Produkt 1

HCID 574445445-[(Benzyloxy)carbonyl]nicotinic acidAusbeute 23,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a suspension of 60% sodium hydride (527 mg) in dimethylformamide (20 mL) was added 3,5-pyridinedicarboxylic acid (2.00 g) under ice-water cooling and the mixture was stirred at 0° C. for 1 hour. To the mixture was added (bromomethyl)benzene (2.05 g) and the mixture was stirred at 60° C. for 2 hours. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with water and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was triturated with ethyl acetate to give 5-[(benzyloxy)carbonyl]nicotinic acid as a pale yellow powder (722 mg).

Aufarbeitung

  1. stirringthe mixture was stirred at 60° C. for 2 hours
  2. customThe mixture was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was triturated with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-7bc9d0b6d129489a9d9f02a62ec13d38
Quelldatensatz
uspto-grants-2008_01
Patentnummer
US07317009B2

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