Water → Ethyl 3-(4-chlorophenyl)-6-difluoromethoxy-4-oxo-3,4-dihydrobenzo[4,5]furo[2,3-d]pyridazine-9-carboxylate

HRID 1091876Notes

Reaction equation

HRID 1091876 reaction equation
[F:1][CH:2]([F:23])[O:3][C:4]1[C:9]2[O:10][C:11]3[C:12](=[O:17])[NH:13][N:14]=[CH:15][C:16]=3[C:8]=2[C:7]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:6][CH:5]=1.Cl.[Cl:25][C:26]1[CH:31]=[CH:30][C:29](NN)=[CH:28][CH:27]=1.C(=O)([O-])[O-].[Na+].[Na+].O>C(O)C>[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([N:13]2[C:12](=[O:17])[C:11]3[O:10][C:9]4[C:4]([O:3][CH:2]([F:1])[F:23])=[CH:5][CH:6]=[C:7]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:8]=4[C:16]=3[CH:15]=[N:14]2)=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)HCID 66592670Ethyl 6-difluoromethoxy-4-oxo-3,4-dihydrobenzo[4,5]furo[2,3-d]pyridazine-9-carboxylate

Product 1

HCID 66593036Ethyl 3-(4-chlorophenyl)-6-difluoromethoxy-4-oxo-3,4-dihydrobenzo[4,5]furo[2,3-d]pyridazine-9-carboxylateYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 6-difluoromethoxy-4-oxo-3,4-dihydrobenzo[4,5]furo[2,3-d]pyridazine-9-carboxylate (from step 6 of example 4) (168 mg, 0.4 mmol) in ethanol (20 ml), p-chloro phenylhydrazine hydrochloride (72 mg, 0.4 mol) and sodium carbonate (43 mg, 0.4 mmol) was added at room temp. The reaction mixture was stirred at room temp. for 4 hrs. Ethanol was distilled out under vacuum. The concentrated mass was heated to reflux temperature in acetic acid. Progress of reaction was monitored by TLC. At the end, water was added, the solid obtained was filtered and suck dried. The solid was dried in oven. White colored solid (160 mg) was obtained.

Workup

  1. distillationEthanol was distilled out under vacuum
  2. temperatureThe concentrated mass was heated
  3. temperatureto reflux temperature in acetic acid
  4. customProgress of reaction
  5. customthe solid obtained
  6. filtrationwas filtered
  7. customsuck dried
  8. customThe solid was dried in oven

Sources & evidence

ORD record
ord-936d30030cee4447a7abb838639bee69
Source dataset
uspto-grants-2012_03
Patent number
US08129401B2

Reaction notes

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