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

HRID 709775Notes

Reaction equation

HRID 709775 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.C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>CN(C=O)C>[CH2:19]([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:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 46941479Methyl 6-chloro-5-hydroxynicotinate

Product 1

HCID 71496987Methyl 5-(benzyloxy)-6-chloronicotinate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 6-chloro-5-hydroxynicotinate (3.71 g) in DMF (30 mL) were added potassium carbonate (5.47 g) and benzyl bromide (2.59 mL), and the mixture was stirred at room temperature for 30 min. Water was added to the reaction mixture at 0° C., and the resulting precipitate was collected by filtration. The obtained crude crystals were washed with water and hexane, and dried at 50° C. for 15 min under reduced pressure to give a crude product of the title compound (4.57 g) as a pale-yellow solid. This compound was used for the next step without further purification.

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. customThe obtained crude crystals
  3. washwere washed with water and hexane
  4. customdried at 50° C. for 15 min under reduced pressure

Sources & evidence

ORD record
ord-e494243bc53f46e5839657613ad8c13c
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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