Hydrazine → HCID 15884729, compound

HRID 379518Notes

Reaction equation

HRID 379518 reaction equation
[CH3:1][O:2][CH2:3][CH:4]1[CH2:8][CH2:7][CH:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH3:16])[N:5]1[CH2:17][CH2:18][N:19]1C(=O)C2=CC=CC=C2C1=O.NN>C(O)C>[CH3:1][O:2][CH2:3][CH:4]1[CH2:8][CH2:7][CH:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH3:16])[N:5]1[CH2:17][CH2:18][NH2:19]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 15884728HCID 15884728, compound

Product 1

HCID 15884729HCID 15884729, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-methoxymethyl-5-(2-methoxyphenyl)-(2-phthalimidoethyl)-tetrahydropyrrole (333 mg, 0.85 mmol) in ethanol (5 mL) was added anhydrous hydrazine (80 μl, 2.5 mmol). The resulting suspension was stirred at room temperature for 3 days. The reaction mixture was filtered through Celite™, and the solid was washed with methanol (40 mL). The filtrate was concentrated in vacuo, the residue was triturated with CH2Cl2 (40 mL) and filtered to remove any remaining byproduct. The filtrated was again concentrated to afford the title compound as a light yellow oil (211 mg). MS m/z: 265 (M+H).

Workup

  1. filtrationThe reaction mixture was filtered through Celite™
  2. washthe solid was washed with methanol (40 mL)
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was triturated with CH2Cl2 (40 mL)
  5. filtrationfiltered
  6. customto remove any remaining byproduct
  7. concentrationThe filtrated was again concentrated

Sources & evidence

ORD record
ord-738eb81fabd8417785bb3a787f6a2610
Source dataset
uspto-grants-2001_10
Patent number
US06300316B1

Reaction notes

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