Hydrazine → HCID 9844212, compound

HRID 1376568Notes

Reaction equation

HRID 1376568 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:28]=[CH:29][CH:30]=1)[O:7][CH2:8][CH2:9][CH2:10][NH:11][CH2:12][CH:13]1[CH2:22][CH2:21][C:20]2[C:15](=[CH:16][C:17]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])=[CH:18][CH:19]=2)[O:14]1)([O-])=O.NN>C(O)C.[Ni]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:28]=[CH:29][CH:30]=1)[O:7][CH2:8][CH2:9][CH2:10][NH:11][CH2:12][CH:13]1[CH2:22][CH2:21][C:20]2[C:15](=[CH:16][C:17]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])=[CH:18][CH:19]=2)[O:14]1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 22917829HCID 22917829, compound

Product 1

HCID 9844212HCID 9844212, compoundYield 69.9%

Reagents, catalysts & solvents 2

HCID 935NickelCatalyst2×HCID 702EthanolSolvent

Procedure

To a mixture of N-(2-{[3-(3-nitro-phenoxy)-propylamino]-methyl}-chroman-7-yl)-methanesulfonamide and hydrazine in ethanol at 5° C. was added Raney nickel (400 mg). After 0.5 hour another portion of Raney nickel (300 mg) was added and the reaction was heated to reflux for 1 hour. The catalyst was filtered and the solvent removed to afford N-(2-{[3-(3-amino-phenoxy)-propylamino]-methyl}-chroman-7-yl)-methanesulfonamide in 69.9% yield. The (2:1)oxalate, hemihydrate was prepared from tetrahydrofuran and triturated in methanol, mp 183°-185° C.

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 1 hour
  3. filtrationThe catalyst was filtered
  4. customthe solvent removed

Sources & evidence

ORD record
ord-75a1ed7e18f6463383087b50ea63a8f5
Source dataset
uspto-grants-1997_09
Patent number
US05663194

Reaction notes

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