2-Methoxy-1-nitronaphthalene → 2-Methoxynaphthalen-1-amine

HRID 1731062Notes

Reaction equation

HRID 1731062 reaction equation
[N+:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][C:5]=1[O:14][CH3:15])([O-])=O>C(O)C.[Ni]>[NH2:1][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][C:5]=1[O:14][CH3:15]

Participants

4

Reactant 1

HCID 786142-Methoxy-1-nitronaphthalene

Product 1

HCID 752522-Methoxynaphthalen-1-amine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

1-nitro-2-methoxynaphthalene (1 g.) is hydrogenated in absolute ethanol (200 ml.) over Raney nickel catalyst (1 g.) at 25° C and an initial pressure of 40 psi until the theoretical amount of hydrogen is absorbed. The catalyst is removed, the filtrate concentrated to dryness under vacuum, and the residue recrystallized from methanol to yield 1-amino-2-methoxynaphthalene.

Workup

  1. customan initial pressure of 40 psi until the theoretical amount of hydrogen is absorbed
  2. customThe catalyst is removed
  3. concentrationthe filtrate concentrated to dryness under vacuum
  4. customthe residue recrystallized from methanol

Sources & evidence

ORD record
ord-797616fef3ab432bad5d5bfe716108b7
Source dataset
uspto-grants-1976_11
Patent number
US03994968

Reaction notes

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