Hydrazine hydrate (1:1) → HCID 22235995, compound

HRID 1744077Notes

Reaction equation

HRID 1744077 reaction equation
[CH3:1][C:2]1([CH3:25])[O:6][C:5](=[O:7])[C:4]([N:8]2C(=O)C3C(=CC=CC=3)C2=O)=[C:3]1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O.NN>C1COCC1.CO.CCOC(C)=O>[NH2:8][C:4]1[C:5](=[O:7])[O:6][C:2]([CH3:1])([CH3:25])[C:3]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 22235805HCID 22235805, compound

Product 1

HCID 22235995HCID 22235995, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a 0° C. solution of 2-(5,5-dimethyl-2-oxo4-phenyl-2,5-dihydro-3-furanyl)-1H-isoindole-1,3(2H)-dione (0.90 g, 2.7 mmol) in THF (40 mL) and MeOH (30 mL) was added hydrazine hydrate (1 mL). The mixture was stirred overnight then diluted with EtOAc and washed with saturated NH4Cl. The organic phase was concentrated, then dissolved in dichloromethane, washed with brine, filtered through cotton and concentrated. This material was combined with the 0.29 g from the previous step and purified by flash chromatography (25% EtOAc/hexanes) to provide 3-amino-5,5-dimethyl-4-phenyl-2(5H)-furanone.

Workup

  1. washwashed with saturated NH4Cl
  2. concentrationThe organic phase was concentrated
  3. dissolutiondissolved in dichloromethane
  4. washwashed with brine
  5. filtrationfiltered through cotton
  6. concentrationconcentrated
  7. custompurified by flash chromatography (25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-b7ebfef6dd6e4244a2072e48ce0dc1fa
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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