Ammonium Hydroxide → 7-nitro-3,4-dihydro-2H-naphthalen-1-one oxime

HRID 636283Notes

Reaction equation

HRID 636283 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][C:11]2=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH4+:15].[OH-:16].CC([O-])=O.[Na+]>C(O)C.O>[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][C:11]2=[N:15][OH:16])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 384457-Nitro-1-tetraloneHCID 517045Sodium Acetate

Product 1

HCID 3000317-nitro-3,4-dihydro-2H-naphthalen-1-one oximeYield 93%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

7-Nitro-1-tetralone (2.00 g, 10.4 mmol) was dissolved in ethanol (20 mL) and was added to NH4OH (1.64 mL, 16.6 mmol) and NaOAc (1.71 g, 20.8 mmol) in H2O (30 mL). After 2 h at 65° C., the solvent was removed under reduced pressure and the residue was titurated with H2O. The precipitate was removed by filtration and dried under vacuum to give 1.99 g (93%) of the desired material as a white solid. MS (ES-) m/z 205 [M−H]−.

Workup

  1. customthe solvent was removed under reduced pressure
  2. customThe precipitate was removed by filtration
  3. customdried under vacuum

Sources & evidence

ORD record
ord-614bb795c2eb44eea47b9baa5f370992
Source dataset
uspto-grants-2001_02
Patent number
US06191146B1

Reaction notes

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