7-Nitro-1-tetralone → NSC174091

HRID 518844Notes

Reaction equation

HRID 518844 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.[NH2:16][OH:17].C([O-])(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(O)C.O>[OH:17]/[N:16]=[C:11]1\[CH2:10][CH2:9][CH2:8][C:7]2[C:12]\1=[CH:13][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2

Participants

7

Reactant 4

HCID 384457-Nitro-1-tetraloneHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 517045Sodium Acetate

Product 1

HCID 9562703NSC174091Yield 21.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 5 g of 7-nitro-3,4-dihydronaphthalen-1(2H)-one, 2.18 g of hydroxylamine hydrochloride, 4.29 g of sodium acetate in 90 ml of ethanol and 90 ml of water is refluxed for one hour. The reaction medium is brought back to ambient temperature and an aqueous 10% sodium bicarbonate solution is added until a pH of 7 is reached. The mixture is extracted with ethyl acetate and the organic phase is dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification is carried out by flash chromatography on silica gel (40-63 μm), elution being carried out with a mixture of heptane and of ethyl acetate (80/20 to 50/50). 1.14 g of (1E)-N-hydroxy-7-nitro-3,4-dihydronaphthalen-1(2H)-imine are obtained in the form of a yellow solid.

Workup

  1. temperatureis refluxed for one hour
  2. customis brought back to ambient temperature
  3. extractionThe mixture is extracted with ethyl acetate
  4. dry with materialthe organic phase is dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification
  8. washis carried out by flash chromatography on silica gel (40-63 μm), elution
  9. additionbeing carried out with a mixture of heptane and of ethyl acetate (80/20 to 50/50)

Sources & evidence

ORD record
ord-db20ec8286a143cf997add74a4a925c5
Source dataset
uspto-grants-2015_08
Patent number
US09115140B2

Reaction notes

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