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

HRID 1654396Notes

Reaction equation

HRID 1654396 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-54cf4d1cb6c84c519137ad634b00a17c
Source dataset
uspto-grants-1995_04
Patent number
US05405851

Reaction notes

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