Trimethylsilyldiazomethane → Methyl 4-chloronicotinate

HRID 1427157Notes

Reaction equation

HRID 1427157 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[C:8]([OH:10])=[O:9].[Si](C=[N+]=[N-])(C)(C)[CH3:12]>ClCCl.CO.CCOCC>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[C:8]([O:10][CH3:12])=[O:9]

Participants

6

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 8182294-Chloronicotinic acid

Product 1

HCID 12574055Methyl 4-chloronicotinate

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 4-chloro-3-pyridinecarboxylic acid (3.630 g) in dichloromethane (20 mL) and methanol (8 mL) stirred under argon at 0° C. was added TMS-diazomethane 2M in Et2O (17.28 mL) dropwise. The reaction mixture was stirred at room temperature for 1 h. The solvents were evaporated in vacuo and the crude product was added to a silica gel column and was eluted with cyclohexane/EtOAc=7/3. The evaporation of the collected fractions gave 2.7 g of the title compound as a colourless solid.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 1 h
  2. customThe solvents were evaporated in vacuo
  3. additionthe crude product was added to a silica gel column
  4. washwas eluted with cyclohexane/EtOAc=7/3
  5. customThe evaporation of the collected fractions

Sources & evidence

ORD record
ord-18485ab104dd44d184e3bcd8d5d8e508
Source dataset
uspto-grants-2015_01
Patent number
US08933132B2

Reaction notes

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