HCID 2974347, compound → HCID 57438148, compound

HRID 230472Notes

Reaction equation

HRID 230472 reaction equation
C([NH:3][C:4]1[CH:9]=[C:8]([N:10]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)[CH:7]=[CH:6][C:5]=1[N+:17]([O-])=O)C.N[C:21]1C=CC(N2CCN(C(OC(C)(C)C)=O)CC2)=C[C:22]=1NCC>[Ni]>[CH3:21][CH2:22][NH:17][C:5]1[C:4]([NH2:3])=[CH:9][C:8]([N:10]2[CH2:11][CH2:12][N:13]([CH3:16])[CH2:14][CH2:15]2)=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 2974347HCID 2974347, compoundHCID 22272508HCID 22272508, compound

Product 1

HCID 57438148HCID 57438148, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

N-Ethyl-5-(4-methyl-1-piperazinyl)-2-nitroaniline was reduced with Raney-Ni as described previously for the synthesis of tert-butyl 4-[4-amino-3-(ethylamino)phenyl]-1-piperazinecarboxylate to give N-2-ethyl-4-(4-methyl-1-piperazinyl)-1,2-benzenediamine (yield >90%) as a red oil. The product is very sensitive to oxidation and was therefore used immediately in the next reaction step. HPLC purity >90%; MS (posEI) m/z=234 (M+);

Sources & evidence

ORD record
ord-306c4832b03a4988b374dada039fd3cb
Source dataset
uspto-grants-2009_07
Patent number
US07566715B2

Reaction notes

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