Hydrazine hydrate (1:1) → HCID 71278717, compound

HRID 1750025Notes

Reaction equation

HRID 1750025 reaction equation
O.[NH2:2][NH2:3].[CH3:4][O:5][C:6]1[CH:15]=[CH:14][C:9]2[C:10](=[O:13])[CH2:11][O:12][C:8]=2[C:7]=1[CH2:16][CH:17]([C:21](=O)[CH3:22])[C:18](=O)[CH3:19].C(=O)([O-])O.[Na+]>O.C(O)(=O)C>[CH3:22][C:21]1[C:17]([CH2:16][C:7]2[C:8]3[O:12][CH2:11][C:10](=[O:13])[C:9]=3[CH:14]=[CH:15][C:6]=2[O:5][CH3:4])=[C:18]([CH3:19])[NH:3][N:2]=1

Participants

6

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 516892Sodium BicarbonateHCID 71278942HCID 71278942, compound

Product 1

HCID 71278717HCID 71278717, compoundYield 81.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of hydrazine monohydrate (0.0102 g, 0.203 mmol) in water (1.25 mL) was cooled to 0° C., and added with a solution of 3-[(6-methoxy-3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]pentane-2,4-dione (0.0533 g, 0.193 mmol) in acetic acid (2 mL), and the mixture was stirred for 18 hours with warming it to room temperature. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate, thereby made basic, and extracted three times with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography (chloroform/methanol) to obtain 7-[(3,5-dimethyl-1H-pyrazol-4-yl)methyl]-6-methoxybenzofuran-3(2H)-one (0.0427 g, 81%).

Workup

  1. extractionextracted three times with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was purified by silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-614f162d792b42aaab0013fc37d4fc19
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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