Hydrochloric Acid → 4-(3-chloro-6-pyridazinyloxy)phenylacetic Acid

HRID 235049

Reaction equation

HRID 235049 reaction equation
[H-].[Na+].[C:3]1([CH2:9][C:10]([OH:12])=[O:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.N1C=[CH:17][CH:16]=[CH:15][N:14]=1.[ClH:19].C[N:21]([CH:23]=[O:24])C>>[Cl:19][C:15]1[N:14]=[N:21][C:23]([O:24][C:6]2[CH:7]=[CH:8][C:3]([CH2:9][C:10]([OH:12])=[O:11])=[CH:4][CH:5]=2)=[CH:17][CH:16]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 999Phenylacetic AcidHCID 6228Dimethylformamide2×HCID 9259PyridazineHCID 24758Sodium hydride

Product 1

HCID 233536214-(3-chloro-6-pyridazinyloxy)phenylacetic Acid

Procedure

To a mixture of 0.54 g (0.013 mol, 2.0 equiv) of 60% sodium hydride/mineral oil dispersion in 10 m of dry DMF was added dropwise at room temperature a solution 1.02 g (0.0067 mol) of the phenylacetic acid in 2.3 mL of DMF. After 15-20 minutes, a solid existed which was difficult to stir. The pyridazine (1.0 g, 0.0067 mol) was then added and the mixture was heated at 60°-65° C. for about 2 hours and was allowed to cool. The mixture was poured onto ice water and was adjusted to pH 5 with 2.0N HCl, and the precipitate was collected. This material was triturated under heptane to afford 880 mg of the title product. MP 124°-127° C.

Workup

  1. temperaturethe mixture was heated at 60°-65° C. for about 2 hours
  2. temperatureto cool
  3. additionThe mixture was poured onto ice water
  4. customthe precipitate was collected
  5. customThis material was triturated under heptane

Sources & evidence

ORD record
ord-7aba8952b0c94c119cf98a1868fbe356
Source dataset
uspto-grants-1997_01
Patent number
US05597836

Linked notes

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