Acetic Anhydride → Acetamide, N-[(1S)-1,2,3,4-tetrahydro-1-naphthalenyl]-

HRID 2072153Notes

Reaction equation

HRID 2072153 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:12](OC(=O)C)(=[O:14])[CH3:13]>C1(C)C=CC=CC=1>[C@@H:1]1([NH:11][C:12](=[O:14])[CH3:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

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

Product 1

HCID 11412833Acetamide, N-[(1S)-1,2,3,4-tetrahydro-1-naphthalenyl]-

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-c54e3b09e0f6464aa4fa14ae972f4d38
Source dataset
uspto-grants-1977_09
Patent number
US04049717

Reaction notes

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