6-Acetyltetralin → HCID 240448, compound

HRID 1737209Notes

Reaction equation

HRID 1737209 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH2:10][CH2:9][CH2:8][CH2:7]2)(=O)[CH3:2].Cl.[NH2:15][OH:16].C([O-])(=O)C.[Na+]>CO>[CH:5]1[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=2[CH:12]=[CH:13][C:4]=1[C:1](=[N:15][OH:16])[CH3:2]

Participants

5

Reactant 3

HCID 698856-AcetyltetralinHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 240448HCID 240448, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6-acetyltetralin (5.0 g, 29 mmol) in methanol (30 mL) under a nitrogen atmosphere was added hydroxylamine hydrochloride (2.18 g, 32 mmol) and sodium acetate (2.59 g, 32 mmol) and the resulting mixture was stirred overnight. The reaction mixture was concentrated under reduced pressure and the residue was taken up in diethyl ether and washed with water and then with saturated sodium chloride solution. The organic phase was dried (MgSO4) and concentrated under reduced pressure to afford an oil which solidified. The solid was pulverized and rinsed with hexanes to afford the title compound of Step C (3.85 g) as an off-white solid. 1H NMR (CDCl3): δ 9.1 (br s,1H), 7.33 (m,2H), 7.07 (d,1H), 2.78 (m,4H), 2.27 (s,3H), 1.79 (m,4H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. washwashed with water
  3. dry with materialThe organic phase was dried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customto afford an oil which
  6. washrinsed with hexanes

Sources & evidence

ORD record
ord-d75298fa066e4607a4de1e42c47a1021
Source dataset
uspto-grants-1999_10
Patent number
US05962436

Reaction notes

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