Acetic Acid → 2-(3-Aminophenyl)naphthalene

HRID 2086788Notes

Reaction equation

HRID 2086788 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[CH:12]=[C:13]([N+:17]([O-])=O)[CH:14]=[CH:15][CH:16]=1.C(O)(=O)C>C(O)C.C(Cl)(Cl)Cl.[Fe]>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[CH:12]=[C:13]([CH:14]=[CH:15][CH:16]=1)[NH2:17]

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 113226332-(3-Nitrophenyl)naphthalene

Product 1

HCID 27601672-(3-Aminophenyl)naphthaleneYield 109.5%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

A mixture of 3-(2-naphthyl)-1-nitrobenzene (5.4 g), iron (3.63 g) and acetic acid (13.0 g) in ethanol (50 ml) was stirred under reflux for 3 hours. The reaction mixture was diluted with chloroform, filtered and treated with saturated sodium bicarbonate solution. The chloroform layer was separated, dried, evaporated and chromatographed on silica gel to give 3-(2-naphthyl)aniline (5.2 g).

Workup

  1. temperatureunder reflux for 3 hours
  2. filtrationfiltered
  3. additiontreated with saturated sodium bicarbonate solution
  4. customThe chloroform layer was separated
  5. customdried
  6. customevaporated
  7. customchromatographed on silica gel

Sources & evidence

ORD record
ord-6b7dfe1c80d94d1d98741347e31b25a0
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

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