Ethylamine → N-Ethyl-1-naphthalenamine

HRID 1833973

Reaction equation

HRID 1833973 reaction equation
[C:1]1(O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.P(OCCCC)(OCCCC)OCCCC.[CH2:28]([NH2:30])[CH3:29].[OH-].[Na+]>>[CH2:28]([NH:30][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)[CH3:29]

Participants

5

Reactant 4

HCID 6341EthylamineHCID 70051-NaphtholHCID 7623Tributyl phosphiteHCID 14798Sodium Hydroxide

Product 1

HCID 67043N-Ethyl-1-naphthalenamineYield 85%

Procedure

288 parts of α-naphthol, 10 parts of tributyl phosphite and 110 parts of ethylamine gas are heated for 20 hours at 240° C, whilst stirring. After cooling and letting down the autoclave, the mixture is stirred for 20 minutes with 1,000 parts of 2.5 percent strength by weight aqueous sodium hydroxide solution at 70° C. The organic phase is separated off, washed with 2,000 parts of water at 30° C, separated off and distilled. 290 parts of N-ethyl-α-naphthylamine boiling at 119° - 120° C/0.1 mm Hg are obtained, corresponding to a yield of 85% of theory.

Workup

  1. temperatureAfter cooling
  2. customThe organic phase is separated off
  3. washwashed with 2,000 parts of water at 30° C
  4. customseparated off
  5. distillationdistilled

Sources & evidence

ORD record
ord-df02dd5d1af64774bcb18913ed6bd0e8
Source dataset
uspto-grants-1978_01
Patent number
US04067903

Linked notes

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