Hydrochloric Acid → Ethyl 2-(5-bromo-4-amino-6-oxopyridazin-1(6H)-yl)acetate

HRID 2092080Notes

Reaction equation

HRID 2092080 reaction equation
[Br:1][C:2]1[C:7](=[O:8])[N:6]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:5]=[CH:4][C:3]=1[NH:15]CC1C=CC(OCC)=C(OC)C=1.Cl>C(O)C>[Br:1][C:2]1[C:7](=[O:8])[N:6]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:5]=[CH:4][C:3]=1[NH2:15]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59574404Ethyl 2-[5-bromo-4-(4-ethoxy-3-methoxybenzylamino)-6-oxopyridazin-1(6H)-yl]acetate

Product 1

HCID 59574360Ethyl 2-(5-bromo-4-amino-6-oxopyridazin-1(6H)-yl)acetateYield 52%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

Ethyl 2-[5-bromo-4-(4-ethoxy-3-methoxybenzylamino)-6-oxopyridazin-1(6H)-yl]acetate (570 mg, 1.29 mmol) in ethanol (11 mL) was stirred with concentrated hydrochloric acid (3.4 mL) at 90° C. for 4 hours. After cooling, the solvent was removed by distillation, and the residue was stirred with ethanol (10 mL) and 4 M hydrogen chloride-1,4-dioxane (1 mL) at 90° C. for 1 hour. After cooling, the solvent was removed by distillation. Toluene was added, and the resulting crystals were collected by filtration as the desired product (184 mg, 52% yield).

Workup

  1. temperatureAfter cooling
  2. customthe solvent was removed by distillation
  3. temperatureAfter cooling
  4. customthe solvent was removed by distillation
  5. additionToluene was added

Sources & evidence

ORD record
ord-9f2fb0c160784ca3b5a300ea24d7fd1f
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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