7-Nitro-1-tetralone → HCID 86584343, compound

HRID 361393Notes

Reaction equation

HRID 361393 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].Cl.[O:16]([NH2:18])[CH3:17].C(=O)(O)[O-].[Na+]>CCO>[CH3:17][O:16][N:18]=[C:11]1[C:12]2[C:7](=[CH:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:13]=2)[CH2:8][CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 384457-Nitro-1-tetraloneHCID 516892Sodium BicarbonateHCID 521874O-Methylhydroxylamine hydrochloride

Product 1

HCID 86584343HCID 86584343, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

7-Nitro-tetralone (1.00 g, 5.23 mmol) was suspended in EtOH (10 mL), cooled by an ice water bath and treated with methoxylamine hydrochloride (0.52 g, 6.23 mmol) and sodium bicarbonate (0.57 g, 6.78 mmol). The mixture was stirred at room temperature for 1 h before ice water (50 mL) was added. A precipitate formed which was filtered off to give a white solid 1.10 g, 95% yield). This solid contained two geometric isomers in a ratio of 7:1. It was dissolved in CCl4 /CHCl3 and flash chromatographed over silica gel (50 g) eluting with EtOAc/hexane (1:20) to afford the major isomer as a white solid. It was recrystallized from hot EtOAc to give colorless crystals (556 mg): mp 128°-131° C.

Workup

  1. temperaturecooled by an ice water bath
  2. additionwas added
  3. customA precipitate formed which
  4. filtrationwas filtered off

Sources & evidence

ORD record
ord-bd5b77682cae4eb497046ab7cbd33546
Source dataset
uspto-grants-1999_02
Patent number
US05866579

Reaction notes

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