Hydrazine hydrate (1:1) → HCID 22011031, compound

HRID 323132Notes

Reaction equation

HRID 323132 reaction equation
[N+:1]([C:4]1[CH:34]=[CH:33][C:7]([C:8]([N:10]([CH3:32])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17][CH2:18][CH2:19][CH2:20][N:21]2C(=O)C3=CC=CC=C3C2=O)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].O.NN>C(O)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([N:10]([CH3:32])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17][CH2:18][CH2:19][CH2:20][NH2:21])=[O:9])=[CH:33][CH:34]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 22010616HCID 22010616, compound

Product 1

HCID 22011031HCID 22011031, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-nitro-N-methyl-N-[2-(3-phthalimidoprop-1-yloxy)phenyl]benzamide (760 mg) in ethanol (15 ml) was added hydrazine hydrate (828 mg) and the solution was stirred at ambient temperature for 1 days. After evaporation in vacuo, the residue was diluted with ethyl acetate and then the organic solution was washed successively with saturated sodium bicarbonate aqueous solution and brine. Drying, filtering and removal of solvents afforded 4-nitro-N-methyl-N-[2-(3-aminoprop-1-yloxy)phenyl]benzamide (422 mg) as a yellow oil.

Workup

  1. customAfter evaporation in vacuo
  2. additionthe residue was diluted with ethyl acetate
  3. washthe organic solution was washed successively with saturated sodium bicarbonate aqueous solution and brine
  4. customDrying
  5. filtrationfiltering
  6. customremoval of solvents

Sources & evidence

ORD record
ord-368176aa554c41f98204e7ab5481fdd8
Source dataset
uspto-grants-2001_04
Patent number
US06211242B1

Reaction notes

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