Methylamine → 2-Naphthalenamine, N-methyl-

HRID 1833966Notes

Reaction equation

HRID 1833966 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]=1O.P(OC1C=CC=CC=1)(OC1C=CC=CC=1)OC1C=CC=CC=1.[CH3:34][NH2:35]>O>[CH3:34][NH:35][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 7540Triphenyl phosphiteHCID 86632-Naphthol

Product 1

HCID 1375052-Naphthalenamine, N-methyl-Yield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

288 parts of β-naphthol, 3 parts of triphenyl phosphite and 80 parts of methylamine gas are heated for 10 hours under pressure at 200° C in a pressure autoclave. The pressure is 40 atmospheres. When the two-phase mixture has cooled, water is added, the batch is stirred for 30 minutes at 70° C and the lower oily phase is separated off and distilled. 305 parts of N-methyl-β-naphthylamine, boiling at 165° - 166° C/12 mm Hg, are obtained. This corresponds to a yield of 97% of theory.

Workup

  1. temperatureWhen the two-phase mixture has cooled
  2. customthe lower oily phase is separated off
  3. distillationdistilled

Sources & evidence

ORD record
ord-34a5f6de98ac4d058ed0906a1e4becc7
Source dataset
uspto-grants-1978_01
Patent number
US04067903

Reaction notes

Loading…