Water → Methyl 5-(benzyloxy)-6-chloronicotinate

HRID 709795Notes

Reaction equation

HRID 709795 reaction equation
[Cl:1][C:2]1[C:11]([OH:12])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1.[H-].[Na+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>CN(C=O)C>[CH2:15]([O:12][C:11]1[C:2]([Cl:1])=[N:3][CH:4]=[C:5]([CH:10]=1)[C:6]([O:8][CH3:9])=[O:7])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 46941479Methyl 6-chloro-5-hydroxynicotinate

Product 1

HCID 71496987Methyl 5-(benzyloxy)-6-chloronicotinateYield 38.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 6-chloro-5-hydroxynicotinate (10.5 g) in DMF (80 mL) was added 60% sodium hydride (2.80 g) at 0° C., and the mixture was stirred at 0° C. for 0.5 hr. Benzyl bromide (10.5 g) was added, and the mixture was stirred at room temperature for 20 hr. The reaction mixture was poured into water, and the precipitate was collected by filtration. The crude crystals were purified by silica gel column chromatography (petroleum ether/THF) to give the title compound (6.00 g) as a white solid.

Workup

  1. stirringthe mixture was stirred at room temperature for 20 hr
  2. filtrationthe precipitate was collected by filtration
  3. customThe crude crystals were purified by silica gel column chromatography (petroleum ether/THF)

Sources & evidence

ORD record
ord-dfd1e4923bb4438c84b11435905ef818
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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