Hydrazine hydrate (1:1) → HCID 53641682, compound

HRID 1380871Notes

Reaction equation

HRID 1380871 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([CH2:9][C:10]([NH:12][CH2:13][CH2:14][CH2:15][N:16]([CH3:31])[CH:17]2[CH2:26][CH2:25][C:24]3[C:19](=[CH:20][C:21]([O:29][CH3:30])=[C:22]([O:27][CH3:28])[CH:23]=3)[CH2:18]2)=[O:11])=[C:4]([N+:32]([O-])=O)[CH:3]=1.O.NN>CO.[Ni]>[NH2:32][C:4]1[CH:3]=[C:2]([Cl:1])[C:7]([Cl:8])=[CH:6][C:5]=1[CH2:9][C:10]([NH:12][CH2:13][CH2:14][CH2:15][N:16]([CH3:31])[CH:17]1[CH2:26][CH2:25][C:24]2[C:19](=[CH:20][C:21]([O:29][CH3:30])=[C:22]([O:27][CH3:28])[CH:23]=2)[CH2:18]1)=[O:11]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 543623941-[2-(4,5-dichloro-2-nitro-phenyl)-1-oxo-ethylamino]-3-[N-methyl-N-(6,7-dimethoxy-1,2,3,4-tetrahydronaphth-2-yl)-amino]-propane

Product 1

HCID 53641682HCID 53641682, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Here, 1-[2-(4,5-dichloro-2-nitro-phenyl)-1-oxo-ethylamino]-3-[N-methyl-N-(6,7-dimethoxy-1,2,3,4-tetrahydronaphth-2-yl)-amino]-propane (15.8 g, 0.031 mol) is dissolved in methanol (300 ml) and mixed with 98% hydrazine hydrate (4.65 ml). Raney nickel (2 g) is added in batches with stirring. Then the mixture is stirred for 2 hours at ambient temperature, the catalyst is filtered off and the filtrate is concentrated by evaporation in vacuo. The viscous residue is purified by column chromatography over alumina N (400 g) [activity II, eluant: methylene chloride and increasing amounts of ethanol (up to 1%]. Yield: 13.9 g. IR spectrum (methylene chloride): 1660 cm-1 (C=O), 1515 cm-1 (Amide-II).

Workup

  1. stirringThen the mixture is stirred for 2 hours at ambient temperature
  2. filtrationthe catalyst is filtered off
  3. concentrationthe filtrate is concentrated by evaporation in vacuo
  4. customThe viscous residue is purified by column chromatography over alumina N (400 g) [activity II, eluant
  5. temperaturemethylene chloride and increasing amounts of ethanol (up to 1%]

Sources & evidence

ORD record
ord-82adc747525c45f0836b7d925f23cf94
Source dataset
uspto-grants-1986_04
Patent number
US04584293

Reaction notes

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