Water → HCID 67072580, compound

HRID 386552Notes

Reaction equation

HRID 386552 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11]/[N:12]=[C:13](\[C:18](=[O:24])[CH2:19][C:20](OC)=[O:21])/[C:14]([O:16][CH3:17])=[O:15])=[CH:7][CH:6]=1)(=[O:4])=[O:3].O>ClC1C=CC=CC=1Cl>[OH:24][C:18]1[C:13]([C:14]([O:16][CH3:17])=[O:15])=[N:12][N:11]([C:8]2[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][CH:7]=2)[C:20](=[O:21])[CH:19]=1

Participants

4

Reactant 2

HCID 962WaterHCID 178500932HCID 178500932, compound

Product 1

HCID 67072580HCID 67072580, compoundYield 49.2%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
180 °C

Procedure

The mixture of (E)-dimethyl 2-(2-(4-(methylsulfonyl)phenyl) hydrazono)-3-oxopentanedioate (7.0 g, 19.6 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 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 reduced pressure to yield 3.13 g (49.1%) of methyl 4-hydroxy-1-(4-(methylsulfonyl)phenyl)-6-oxo-1,6-dihydropyridazine-3-carboxylate. MS (ESI) 325 (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 under reduced pressure

Sources & evidence

ORD record
ord-ee7fc753ec5249b884390ecb63c3347c
Source dataset
uspto-grants-2013_02
Patent number
US08372837B2

Reaction notes

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