Hydrochloric Acid → Ethyl Pyridazine-4-carboxylate

HRID 426267

Reaction equation

HRID 426267 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:10])=[O:9])=[CH:4][N:3]=1.[CH2:11](O)[CH3:12]>>[CH2:11]([O:9][C:8]([C:5]1[CH:6]=[CH:7][N:2]=[N:3][CH:4]=1)=[O:10])[CH3:12]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 2761046Pyridazine-4-carboxylic Acid

Product 1

HCID 10855652Ethyl Pyridazine-4-carboxylateYield 49%

Procedure

In a 250 mL round bottom flask, 1 mL concentrated HCl and 70 mL ethanol was added to pyridazine-4-carboxylic acid (3.78 g, 30.4 mmol). The mixture was refluxed overnight. The reaction was 80% complete based on HPLC. The reaction mixture was concentrated down. The residue was purified (silica gel, 2-10% MeOH/DCM) to give light yellow oil (1.8 g, 49%). 1H NMR (300 MHz, CD3OD): δ 9.62 (s, 1H), 9.43 (d, 1H), 8.08 (d, 1H), 4.52 (dd, 2H), 1.43 (t, 3H).

Workup

  1. temperatureThe mixture was refluxed overnight
  2. concentrationThe reaction mixture was concentrated down
  3. customThe residue was purified (silica gel, 2-10% MeOH/DCM)

Sources & evidence

ORD record
ord-16f1bb33b8a148a9b6ca529f0525bc89
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Linked notes

Loading…