Benzoic Acid → Ammonia

HRID 597723Notes

Reaction equation

HRID 597723 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O)([O-:3])=[O:2].[N+:12]([CH2:15][CH3:16])([O-:14])=[O:13].[C:17](O)(=O)C1C=CC=CC=1.[NH:26]1CCC[CH2:28][CH2:27]1>C1(C)C=CC=CC=1.N1C=CC=CC=1.[Ni].CO>[N+:1]([C:4]1[CH:5]=[C:6]([CH2:7][CH:15]([N+:12]([O-:14])=[O:13])[CH3:16])[CH:9]=[CH:10][CH:11]=1)([O-:3])=[O:2].[CH4:17].[NH3:26].[NH2:1][C:4]1[CH:5]=[C:6]([CH2:7][CH:27]([NH2:26])[CH3:28])[CH:9]=[CH:10][CH:11]=1

Participants

12

Reactant 4

HCID 243Benzoic AcidHCID 6587NitroethaneHCID 74493-NitrobenzaldehydeHCID 8082Piperidine

Product 4

HCID 222AmmoniaHCID 297MethaneHCID 149291261-(m-Nitro-phenyl)-2-nitro-propaneHCID 204423703-(2-Aminopropyl)aniline

Reagents, catalysts & solvents 4

HCID 935NickelCatalystHCID 887MethanolSolventHCID 1049PyridineSolventHCID 1140TolueneSolvent

Procedure

1-(m-Nitro-phenyl)-2-nitro-propane (m.p. 56°-58° C.) was prepared by refluxing m-nitro-benzaldehyde and nitroethane in toluene in the presence of benzoic acid and piperidine for 5 hours. The product was then hydrogenated, first in the presence of palladized charcoal in pyridine at 5 atmospheres and room temperature and then in the presence of Raney nickel and ammonia in methanol at 5 atmospheres and 40° C., to form 1-(m-amino-phenyl)-2-amino-propane (b.p. 120°-141° C. at 0.1 mm Hg; m.p. 78°-79° C.).

Sources & evidence

ORD record
ord-ce8b1cef656145d6acc4930174b530b3
Source dataset
uspto-grants-1977_03
Patent number
US04015011

Reaction notes

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