Nitric Acid → 5-Aminoacenaphthene

HRID 46612

Reaction equation

HRID 46612 reaction equation
[N+:1]([C:4]1[C:14]2[C:15]3[C:7]([CH2:8][CH2:9][C:10]=3[CH:11]=[CH:12][CH:13]=2)=[CH:6][CH:5]=1)([O-])=O.C1C2=C3C(=CC=C2)C=CC=C3C1.[N+]([O-])(O)=O.[Sn].NN>Cl.[Ni].C(O)C.C(O)(=O)C>[NH2:1][C:4]1[C:14]2[C:15]3[C:7]([CH2:8][CH2:9][C:10]=3[CH:11]=[CH:12][CH:13]=2)=[CH:6][CH:5]=1

Participants

10

Reactant 5

HCID 944Nitric AcidHCID 6734AcenaphtheneHCID 9321HydrazineHCID 117695-NitroacenaphtheneHCID 5352426Tin atom

Product 1

HCID 625475-Aminoacenaphthene

Reagents, catalysts & solvents 4

HCID 935NickelCatalystHCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

5-Nitroacenaphthene is made by nitrating acenaphthene with nitric acid in the presence of acetic acid according to the method of Rowe and Davies, J. Chem. Soc. 117, 1346 (1920). Standard reduction methods using tin or stannous chloride in hydrochloric acid or by using Raney nickel with ethanol or hydrazine produces 5-aminoacenaphthene.

Sources & evidence

ORD record
ord-1a06f9ffbc2c46afaf47b657be09d7f6
Source dataset
uspto-grants-1979_11
Patent number
US04174342

Linked notes

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