Oxalyl chloride → Methyl 6-chloropyridazine-3-carboxylate

HRID 1714862Notes

Reaction equation

HRID 1714862 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.[C:11](Cl)(=O)C(Cl)=O>ClCCl.C(OCC)(=O)C.CN(C=O)C>[Cl:1][C:2]1[N:7]=[N:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 65578Oxalyl chlorideHCID 64157626-chloropyridazine-3-carboxylic Acid

Product 1

HCID 12379801Methyl 6-chloropyridazine-3-carboxylate

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 6-chloropyridazine-3-carboxylic acid (4.2 g, 26.5 mmol) in a mixture of dichloromethane (100 mL) and ethyl acetate (30 mL) and a few drops of DMF was added oxalyl chloride (3 mL, 34 mmol). The mixture was stirred at room temperature for 4 h until solution was attained, then quenched with 20 mL of methanol. After 15 min, the mixture was concentrated, and the resulting solid was swirled in ether and filtered. The solid was triturated with dichloromethane and the filtrate was evaporated to provide the title compound. 1H NMR (400 MHz, acetone-d6): δ 4.04 (s, 3H), 8.05 (d, 1H), 8.31 (d, 1H).

Workup

  1. customquenched with 20 mL of methanol
  2. waitAfter 15 min
  3. concentrationthe mixture was concentrated
  4. filtrationfiltered
  5. customThe solid was triturated with dichloromethane
  6. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-ee6c3bc2b8e748f291bcefef1821675f
Source dataset
uspto-grants-2010_09
Patent number
US07799787B2

Reaction notes

Loading…