Water → HCID 10267209, compound

HRID 981165Notes

Reaction equation

HRID 981165 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:15]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:13]=[N:12][C:11]=2[C:22](OCC)=[O:23])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[BH4-].[Na+].C(OCC)(=O)C.O>C(O)C.O1CCCC1>[OH:23][CH2:22][C:11]1[N:12]=[N:13][C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:15][C:10]=1[C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 10020712HCID 10020712, compound

Product 1

HCID 10267209HCID 10267209, compoundYield 21.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 4-(3-nitrophenyl)-6-phenyl-3-pyridazinecarboxylate (1 g) in a mixture of ethanol (10 ml) and tetrahydrofuran (10, ml) was added sodium borohydride (0.22 g) and the mixture was stirred for 3 hours at ambient temperature. Then the reaction mixture was poured into a mixture of ethyl acetate (100 ml) and water (50 ml). The organic layer was washed with saturated aqueous sodium chloride, dried over magnesium sulfate and evaporated in vacuo. The residue was subjected to a column chromatography on silica gel (50 g) and eluted with a mixture of benzene and ethyl acetate (5:1 V/V). The fractions containing the desired compound were combined and concentrated under reduced pressure. The residue was recrystallized from a mixture of ethanol and chloroform to give 3-hydroxymethyl-4-(3-nitrophenyl)-6-phenylpyridazine (0.19 g).

Workup

  1. washThe organic layer was washed with saturated aqueous sodium chloride
  2. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo
  4. washeluted with a mixture of benzene and ethyl acetate (5:1 V/V)
  5. additionThe fractions containing the desired compound
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was recrystallized from a mixture of ethanol and chloroform

Sources & evidence

ORD record
ord-1ed4917e2ca0431f87bf680d27320a16
Source dataset
uspto-grants-1991_02
Patent number
US04990507

Reaction notes

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