Hydrazine → HCID 58110125, compound

HRID 1803221Notes

Reaction equation

HRID 1803221 reaction equation
O=[C:2]([CH2:13][CH2:14][CH2:15][C:16]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[O:20][CH2:19][CH2:18][O:17]1)[CH2:3][C:4]([NH:6]C1C=CC=CC=1)=[O:5].[NH2:27]N>C1COCC1>[C:21]1([C:16]2([CH2:15][CH2:14][CH2:13][C:2]3[CH2:3][C:4](=[O:5])[NH:6][N:27]=3)[O:20][CH2:19][CH2:18][O:17]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 86649925HCID 86649925, compound

Product 1

HCID 58110125HCID 58110125, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Step AAH (5): To a soln of 3-oxo-N-phenyl-6-(2-phenyl-1,3-dioxolan-2-yl)hexanamide (444 mg, 1.256 mmol) in THF (1 mL) was added hydrazine (0.059 mL, 1.88 mmol). The mixture was stirred at rt for 2 h, then at 65° C. for 2 h. The reaction mixture was concentrated in vacuo. Dichloromethane (10 mL) was added to the crude residue. After cooling to 0° C., the product crystallized out. The solid was collected by vacuum filtration and dried under high vacuum to afford 3-(3-(2-phenyl-1,3-dioxolan-2-yl)propyl)-1H-pyrazol-5(4H)-one (250 mg, 73% yield). LC-MS (M+H)+ 275.1.

Workup

  1. waitat 65° C. for 2 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additionDichloromethane (10 mL) was added to the crude residue
  4. temperatureAfter cooling to 0° C.
  5. customthe product crystallized out
  6. filtrationThe solid was collected by vacuum filtration
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-32dbbdafaa6943e5abeb1c5c2be1f5ef
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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