Trimethyl orthoacetate → Methyl 5,6-Dichloronicotinate

HRID 217470Notes

Reaction equation

HRID 217470 reaction equation
[Cl:1][C:2]1[C:3]([Cl:11])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[CH3:12]OC(OC)(OC)C>CCOC(C)=O>[Cl:1][C:2]1[C:3]([Cl:11])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([O:9][CH3:12])=[O:8]

Participants

4

Reactant 2

HCID 15050Trimethyl orthoacetateHCID 2479875,6-Dichloronicotinic acid

Product 1

HCID 2782166Methyl 5,6-Dichloronicotinate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 5,6-dichloronicotinic acid (2.2 g) was added 1,1,1-trimethoxyethane (4.3 mL), followed by irradiation with microwave at 120° C. for 15 minutes. The reaction mixture was dissolved in EtOAc and washed with water. The organic layer was dried over MgSO4 and the vehicle was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:EtOAc=85:15 to 80:20) to obtain methyl 5,6-dichloronicotinate (2.2 g) as a white solid.

Workup

  1. customfollowed by irradiation with microwave at 120° C. for 15 minutes
  2. washwashed with water
  3. dry with materialThe organic layer was dried over MgSO4
  4. customthe vehicle was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:EtOAc=85:15 to 80:20)

Sources & evidence

ORD record
ord-8e51362fa5d44881a68264b9487a6ff4
Source dataset
uspto-grants-2012_06
Patent number
US08193378B2

Reaction notes

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