Water → Phenyl 1-(4-Chlorophenyl)-1,4-dihydro-4-oxo-6-methylpyridazine-3-carboxylate

HRID 543052Notes

Reaction equation

HRID 543052 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13]([CH3:14])=[CH:12][C:11](=[O:15])[C:10]([C:16]([OH:18])=[O:17])=[N:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:26]1(O)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.O>C1(C)C=CC=CC=1.CCCCCC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13]([CH3:14])=[CH:12][C:11](=[O:15])[C:10]([C:16]([O:18][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:17])=[N:9]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 996PhenolHCID 8471TriethylamineHCID 197225Fenridazon

Product 1

HCID 9192006Phenyl 1-(4-Chlorophenyl)-1,4-dihydro-4-oxo-6-methylpyridazine-3-carboxylateYield 19.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8058HexaneSolvent

Procedure

To an ice cooled suspension of 5.29 g (0.02 mol) 1-(4-chlorophenyl)-1,4-dihydro-4-oxo-6-methyl pyridazine-3-carboxylic Acid (see Example 12) and 2.02 g (0.02 mol) of triethylamine in 125 ml of toluene there is added dropwise 3.13 g (0.02 mol) of phenyl chlorofomate. The suspension formed is stirred at room temperature for 15 minutes and to it there is added 1.88 g (0.02 mol) of phenol in 25 ml of toluene. The mixture is stirred at room temperature for 18 hrs. and to it there is added 100 ml of water. The suspension is stirred at room temperature for 2 hrs. and is poured into 800 ml of hexane. The suspension formed is stirred at room temperature for 3 hrs. and is vacuum filtered. The filter cake is slurried in 25 ml of toluene and is filtered. The filtrate is added to 150 ml of hexane and the suspension formed is stirred at room temperature for 2 hrs. The suspension is vacuum filtered and the filter cake air dried to afford 1.3 g (19% yield) of product, mp 140°-146° C.

Workup

  1. additionthere is added dropwise 3.13 g (0.02 mol) of phenyl chlorofomate
  2. customThe suspension formed
  3. stirringThe mixture is stirred at room temperature for 18 hrs
  4. stirringThe suspension is stirred at room temperature for 2 hrs
  5. customThe suspension formed
  6. stirringis stirred at room temperature for 3 hrs
  7. filtrationfiltered
  8. filtrationis filtered
  9. additionThe filtrate is added to 150 ml of hexane
  10. customthe suspension formed
  11. stirringis stirred at room temperature for 2 hrs
  12. filtrationfiltered
  13. customthe filter cake air dried

Sources & evidence

ORD record
ord-57e33cddfbd445fba7ba3ddce2647e99
Source dataset
uspto-grants-1987_04
Patent number
US04661145

Reaction notes

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