1,2,3,4-Tetrahydro-4-methylnaphthalen-1-one → HCID 58794254, compound

HRID 1034456Notes

Reaction equation

HRID 1034456 reaction equation
[CH3:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=O)[CH2:4][CH2:3]1.Cl.[NH2:14][OH:15].C(=O)(O)[O-].[Na+]>CO>[CH3:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[N:14][OH:15])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 892321,2,3,4-Tetrahydro-4-methylnaphthalen-1-oneHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 58794254HCID 58794254, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 801 mg (5.0 mmol) of 4-methyl-1-tetralone in 20 mL of dry methanol was treated with 417 mg of hydroxylamine hydrochloride (6.0 mmol, 1.2 eq) and 504 mg (6.0 mmol, 1.2 eq) of sodium bicarbonate and the resulting mixture was stirred at room temperature for 16 hours. The solid was filtered off and the solvent was removed under vacuum. The white residue was redissolved in 10 mL of methylene chloride and filtered. The filtrate was evaporated to dryness under vacuum to give the product in quantitative yield. 1H NMR (400 MHz, CDCl3): 1.30 (d, 8 Hz, 3H), 1.69 (m, 1H), 2.45 (m, 1H), 2.88 (m, 3H), 7.15-7.35 (m, 3H), 7.86 (d, 8 Hz, 1H).

Workup

  1. filtrationThe solid was filtered off
  2. customthe solvent was removed under vacuum
  3. dissolutionThe white residue was redissolved in 10 mL of methylene chloride
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness under vacuum
  6. customto give the product in quantitative yield

Sources & evidence

ORD record
ord-29f9d9839f2841faa3aa057d16fc014e
Source dataset
uspto-grants-1994_05
Patent number
US05317017

Reaction notes

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