Water → Methyl 1-(3,4-dichlorophenyl)-4-hydroxy-6-oxo-1,6-dihydropyridazine-3-carboxylate

HRID 386546Notes

Reaction equation

HRID 386546 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9]/[N:10]=[C:11](\[C:16](=[O:22])[CH2:17][C:18](OC)=[O:19])/[C:12]([O:14][CH3:15])=[O:13])[CH:5]=[CH:6][C:7]=1[Cl:8].O>ClC1C=CC=CC=1Cl>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:18](=[O:19])[CH:17]=[C:16]([OH:22])[C:11]([C:12]([O:14][CH3:15])=[O:13])=[N:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 962WaterHCID 178500929HCID 178500929, compound

Product 1

HCID 54724062Methyl 1-(3,4-dichlorophenyl)-4-hydroxy-6-oxo-1,6-dihydropyridazine-3-carboxylateYield 61.3%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

(E)-Dimethyl 2-(2-(3,4-dichlorophenyl)hydrazono)-3-oxopentanedioate (6.7 g, 19.3 mmol) in 1, 2 dichlorobenzene (20 mL) was heated at 180° C. overnight. After cooling, the reaction to room temperature, water 50 mL was added to the reaction mixture and it was stirred for 1 hour. The product was collected by filtration and further washed with water 20 mL and methanol (10 mL×3), then dried overnight under reduce pressure to yield 3.73 g (55.2%) of methyl 1-(3,4-dichlorophenyl)-4-hydroxy-6-oxo-1,6-dihydropyridazine-3-carboxylate as a tan solid. MS (ESI) 315 (M+H).

Workup

  1. temperatureAfter cooling
  2. customthe reaction to room temperature
  3. filtrationThe product was collected by filtration
  4. washfurther washed with water 20 mL and methanol (10 mL×3)
  5. customdried overnight

Sources & evidence

ORD record
ord-8ea37b3b9f9d4af393f64b9f2c0bbdc3
Source dataset
uspto-grants-2013_02
Patent number
US08372837B2

Reaction notes

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