Ethylene Glycol → trans-1,2,3,4-Tetrahydro-4-methoxy-1-naphthylamine

HRID 372284Notes

Reaction equation

HRID 372284 reaction equation
[CH3:1][O:2][C@H:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C@H:6]([NH:13]C(=O)C)[CH2:5][CH2:4]1.[OH-].[K+].C(O)CO>O>[CH3:1][O:2][C@H:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C@H:6]([NH2:13])[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 14797Potassium HydroxideHCID 70617063trans-N-(1,2,3,4-tetrahydro-4-methoxy-1-naphthyl)acetamide

Product 1

HCID 70617223trans-1,2,3,4-Tetrahydro-4-methoxy-1-naphthylamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 6.9 g. of cis and trans-N-(1,2,3,4-tetrahydro-4-methoxy-1-naphthyl)acetamide, 56.11 g. of potassium hydroxide, 50 ml. of ethylene glycol and 20 ml. of water is stirred and heated at reflux for an overnight period. The mixture is cooled, 100 ml. of water is added and the mixture extracted with methylene chloride (3 × 50 ml.). The combined extract was washed with 125 ml. of 10% sodium hydroxide solution, dried and evaporated in vacuo to afford 5.7 g. of title product - an oil. This oily amine is used without further purification for the preparation of the urea derivative.

Workup

  1. additionA mixture of 6.9 g
  2. temperatureheated
  3. temperatureat reflux for an overnight period
  4. temperatureThe mixture is cooled
  5. extractionthe mixture extracted with methylene chloride (3 × 50 ml.)
  6. extractionThe combined extract
  7. washwas washed with 125 ml
  8. dry with materialof 10% sodium hydroxide solution, dried
  9. customevaporated in vacuo
  10. customto afford 5.7 g
  11. customThis oily amine is used without further purification for the preparation of the urea derivative

Sources & evidence

ORD record
ord-803ae11c6eba462ea04c80813ae580f8
Source dataset
uspto-grants-1978_05
Patent number
US04089976

Reaction notes

Loading…