6-Amino-1,2,3,4-tetrahydronaphthalen-1-one → 6-Amino-3,4-dihydro-2H-naphthalen-1-one oxime

HRID 1040585Notes

Reaction equation

HRID 1040585 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=O)[CH2:7][CH2:6][CH2:5]2.Cl.[NH2:14][OH:15].C([O-])(=O)C.[Na+]>C(O)C.O>[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[N:14][OH:15])[CH2:7][CH2:6][CH2:5]2

Participants

6

Reactant 3

HCID 3395376-Amino-1,2,3,4-tetrahydronaphthalen-1-oneHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 766439426-Amino-3,4-dihydro-2H-naphthalen-1-one oximeYield 83%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

6-Aminotetralone (1.98 g, 12.3 mmol), hydroxylamine hydrochloride (0.85 g, 12.3 mmol), sodium acetate (2.52 g, 30.7 mmol), and water (3.3 ml) were dissolved in ethanol (10 ml), and the mixture was heated to reflux 4 hours. After cooling to room temperature, the mixture was diluted with water (20 ml), and the resulting precipitate was filtered to obtain 6-Amino-3,4-dihydro-2H-naphthalen-1-one oxime as a light brown solid, 1.80 g. (83% yield) 1H NMR (400 MHz, DMSO-d6) δ 10.41 (s, 1H), 7.48-7.53 (m, 1H), 6.36-6.40 (m, 1H), 6.27 (s, 1H), 5.20 (s, 2H), 2.44-2.53 (m, 4H), 1.60-1.69 (m, 2H); MS (m/e) 177 (M+1).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux 4 hours
  3. filtrationthe resulting precipitate was filtered

Sources & evidence

ORD record
ord-80a60252038146d2b05927529099090b
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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