Methane → 5-methoxynaphthalen-1-amine

HRID 1719863Notes

Reaction equation

HRID 1719863 reaction equation
O.NN.[CH3:4][O:5][C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[CH:8]=[CH:9][CH:10]=[C:11]2[N+:16]([O-])=O.C.NN>C(O)C>[NH2:16][C:11]1[C:12]2[C:7](=[C:6]([O:5][CH3:4])[CH:15]=[CH:14][CH:13]=2)[CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 297Methane2×HCID 9321HydrazineHCID 24654Hydrazine hydrate (1:1)HCID 127385811-Methoxy-5-nitronaphthalene

Product 1

HCID 2355485-methoxynaphthalen-1-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

Hydrazine hydrate (150 ml) is added slowly to a stirred mixture of 5-methoxy-1-nitro-naphthalene (320 g), and palladized charcoal (0.1 g) in 95% ethanol (2 liters) previously warmed to 50° C. When the hydrazine addition is complete, additional palladized charcoal (0.1 g) is added and the mixture heated to reflux for about one hour. The reaction mixture is filtered through Celite and the filtrate evaporated in vacuo resulting in a white solid which is recrystallized from H2O and ethanol.

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for about one hour
  3. filtrationThe reaction mixture is filtered through Celite
  4. customthe filtrate evaporated in vacuo
  5. customresulting in a white solid which
  6. customis recrystallized from H2O and ethanol

Sources & evidence

ORD record
ord-e95988124cf644d59d2bc3b9b51a4a22
Source dataset
uspto-grants-1985_09
Patent number
US04543352

Reaction notes

Loading…