Hydrazine → HCID 178451520, compound

HRID 1020878Notes

Reaction equation

HRID 1020878 reaction equation
[NH2:1]N.C[N:4](/[CH:6]=[C:7]1/[CH2:8][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:10][C:11]/1=O)C>C(O)C>[N:1]1[NH:4][CH:6]=[C:7]2[CH2:8][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:10][C:11]=12

Participants

4

Reactant 2

HCID 9321HydrazineHCID 56971730(Z)-tert-butyl 3-((dimethylamino)methylene)-4-oxopyrrolidine-1-carboxylate

Product 1

HCID 178451520HCID 178451520, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of hydrazine (3 mL) and tert-butyl (3Z)-3-[(dimethylamino)methylene]-4-oxopyrrolidine-1-carboxylate (19.22 g) in ethanol (40 mL) was heated at 85° C. in a sealed tube for 4 h. Solvent was removed under reduced pressure, and the residue was triturated with dichloromethane (160 mL) and ethyl acetate (15 mL). The resulting solid was filtered. The filtrate was concentrated and the resulting solid was triturated again and filtered. The combined solids were used without further purification. LC/MS: 210.1 (M+1).

Workup

  1. customSolvent was removed under reduced pressure
  2. customthe residue was triturated with dichloromethane (160 mL) and ethyl acetate (15 mL)
  3. filtrationThe resulting solid was filtered
  4. concentrationThe filtrate was concentrated
  5. customthe resulting solid was triturated again
  6. filtrationfiltered
  7. customThe combined solids were used without further purification

Sources & evidence

ORD record
ord-584ad02925f049f3a4e14ec326c9b438
Source dataset
uspto-grants-2014_05
Patent number
US08716482B2

Reaction notes

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