Sodium Hydroxide → 3-(4-Chlorophenyl)-6-difluoromethoxy-4-oxo-3,4-dihydrobenzo[4,5]furo[2,3-d]pyridazine-9-carboxylic acid

HRID 1091877Notes

Reaction equation

HRID 1091877 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[C:12]3[O:15][C:16]4[C:21]([O:22][CH:23]([F:25])[F:24])=[CH:20][CH:19]=[C:18]([C:26]([O:28]CC)=[O:27])[C:17]=4[C:11]=3[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[C:12]3[O:15][C:16]4[C:21]([O:22][CH:23]([F:25])[F:24])=[CH:20][CH:19]=[C:18]([C:26]([OH:28])=[O:27])[C:17]=4[C:11]=3[CH:10]=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66593036Ethyl 3-(4-chlorophenyl)-6-difluoromethoxy-4-oxo-3,4-dihydrobenzo[4,5]furo[2,3-d]pyridazine-9-carboxylate

Product 1

HCID 665930313-(4-Chlorophenyl)-6-difluoromethoxy-4-oxo-3,4-dihydrobenzo[4,5]furo[2,3-d]pyridazine-9-carboxylic acidYield 95.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of ethyl 3-(4-chlorophenyl)-6-difluoromethoxy-4-oxo-3,4-dihydrobenzo[4,5]furo[2,3-d]pyridazine-9-carboxylate (from step I) (160 mg, 0.36 mmol) and sodium hydroxide (24 mg, 0.51 mmol) in methanol (10 ml) was heated to reflux temp. Progress of reaction was monitored by TLC. At the end, reaction mixture was concentrated under vacuum. Then water (50 ml) was added to reaction mixture and acidified with dilute HCl. The precipitate obtained was filtered and dried in oven. 140 mg yellow colored solid was obtained.

Workup

  1. temperaturewas heated
  2. temperatureto reflux temp
  3. customProgress of reaction
  4. customAt the end, reaction mixture
  5. concentrationwas concentrated under vacuum
  6. additionThen water (50 ml) was added to reaction mixture
  7. customThe precipitate obtained
  8. filtrationwas filtered
  9. customdried in oven

Sources & evidence

ORD record
ord-744eeff19f614f01a16a85f5b7a4d3bd
Source dataset
uspto-grants-2012_03
Patent number
US08129401B2

Reaction notes

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