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

HRID 1657533Notes

Reaction equation

HRID 1657533 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-822e82820ec24ab4b7975a8266820d49
Source dataset
uspto-grants-1976_06
Patent number
US03960957

Reaction notes

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