Acetic Anhydride → (S)-N-(1,2,3,4-tetrahydro-1-naphthyl-1-naphthyl)acetamide

HRID 372398

Reaction equation

HRID 372398 reaction equation
[C@@H:1]1([NH2:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.C(O[C:16](=[O:18])[CH3:17])(=O)C>C1(C)C=CC=CC=1>[C@@H:9]1([C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:1]=2[NH:11][C:16](=[O:18])[CH3:17])[C:10]2[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=2)[CH2:6][CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 70580741-Aminotetralin, (S)-

Product 1

HCID 70619608(S)-N-(1,2,3,4-tetrahydro-1-naphthyl-1-naphthyl)acetamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

(S)-1,2,3,4-tetrahydro-1-naphthylamine (26.9 g.) is dissolved in 200 ml. of toluene and 36 g. of acetic anhydride is added while the temperature from the reaction exotherm is moderated at 50° C. to 60° C. with an ice-bath. The solution is heated to reflux for 0.5 hr. and then stirred at room temperature overnight. The mixture is then evaporated to dryness and the residue is washed well with ether. On drying, 26.1 g. of the title compound, m.p. 153° C. to 155° C., is obtained.

Workup

  1. customis moderated at 50° C. to 60° C. with an ice-bath
  2. temperatureThe solution is heated
  3. temperatureto reflux for 0.5 hr
  4. customThe mixture is then evaporated to dryness
  5. washthe residue is washed well with ether
  6. customOn drying

Sources & evidence

ORD record
ord-e4665fed39504738b9c5d341cd336482
Source dataset
uspto-grants-1978_05
Patent number
US04091018

Linked notes

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