Acetic Anhydride → 1-Acetamido-5,6,7,8-tetrahydronaphthalene

HRID 2258706Notes

Reaction equation

HRID 2258706 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[NH2:8][C:9]1[C:18]2[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=2[CH:12]=[CH:11][CH:10]=1>CCCCCC>[C:9]1([NH:8][C:5](=[O:7])[CH3:6])[C:18]2[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=2[CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 166715-Tetralinylamine

Product 1

HCID 2320651-Acetamido-5,6,7,8-tetrahydronaphthaleneYield 71.5%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Acetic anhydride (100 ml, 1.06 mole) was added rapidly to neat 1-amino-5,6,7,8-tetrahydronaphthalene (25 g, 0.17 mole) (Aldrich) with stirring. The mixture quickly solidified and was allowed to stand overnight. The broken mass was suspended in hexane (200 ml), filtered, then resuspended in methylene chloride (150 ml). After stirring 10 minutes, the suspension was diluted with an equal volume of hexane, filtered, and the solid dried at 95° C. under reduced pressure to give N-(5,6,7,8-tetrahydro-1-naphthyl)acetamide (23 g). 1H NMR (CDCl3, 200 MHz) δ: 1.68-1.90 (m, 4H, CH2 's), 2.20 (s, 3H, CH3), 2.52-2.68 (m, 2H, ArCH2), 2.70-2.84 (m, 2H, ArCH2), 3.94 (br s, 1H, NH), 6.92 (d, J=8 Hz, 1H, Ar), 7.10 (t, J=8 Hz, 1H, Ar), 7.53 (d, J=8 Hz, 1H, Ar). Anal. Calculated for C12H15NO: C, 76.16; H, 7.99; N, 7.40. Found: C, 76.13; H, 8.04; N, 7.40.

Workup

  1. filtrationfiltered
  2. stirringAfter stirring 10 minutes
  3. additionthe suspension was diluted with an equal volume of hexane
  4. filtrationfiltered
  5. customthe solid dried at 95° C. under reduced pressure

Sources & evidence

ORD record
ord-c75a5847b2444bb3a331e613c778eef9
Source dataset
uspto-grants-1997_08
Patent number
US05661155

Reaction notes

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