Hydroxylamine → 7-Methoxy-1-tetralone Oxime

HRID 2173669Notes

Reaction equation

HRID 2173669 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH2:9][C:10]2=O)=[CH:5][CH:4]=1.[NH2:14][OH:15]>CO.CC(O)=O>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH2:9][C:10]2=[N:14][OH:15])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 787HydroxylamineHCID 812767-Methoxy-1,2,3,4-tetrahydronaphthalen-1-one

Product 1

HCID 573710067-Methoxy-1-tetralone Oxime

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of 7-methoxytetralone (15 g) in MeOH (175 mL), NH2OH (50% in H2O, 15.7 mL) and AcOH (4 mL) was added. After stirring for 1 hour, the solution was concentrated until a solid began to appear. The reaction was poured into dilute aqueous NaHCO3 (500 mL), and the resulting solid was filtered to provide the title compound (17.8 g): 1H NMR (DMSO-d6) δ 11.08 (s, 1H), 7.35 (s, 1H), 7.08 (d, 1H), 6.84 (d, 1H), 3.71 (s, 3H), 2.62-2.49 (m, 4H), 1.77-1.64 (m, 2H).

Workup

  1. concentrationthe solution was concentrated until a solid
  2. additionThe reaction was poured into dilute aqueous NaHCO3 (500 mL)
  3. filtrationthe resulting solid was filtered

Sources & evidence

ORD record
ord-3fb1d5ac0b524bd98048f03f48ec6a3f
Source dataset
uspto-grants-2015_06
Patent number
US09056885B2

Reaction notes

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