Sodium Carbonate → HCID 6514828, compound

HRID 1375352Notes

Reaction equation

HRID 1375352 reaction equation
CO[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH2:8][CH2:7][CH2:6]2.Cl.[NH2:15][OH:16].[C:17](=O)([O-])[O-].[Na+].[Na+]>C(O)C>[CH3:17][O:13][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[CH2:11][CH2:12][CH2:3]/[C:4]/2=[N:15]/[OH:16]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 141126-Methoxy-alpha-tetraloneHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 6514828HCID 6514828, compoundYield 97.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 6-methoxy-1-tetralone (5.0 g) in ethanol (100 mL) was treated with hydroxylamine hydrochloride (2.0 g) and sodium carbonate (3.6 g). The reaction mixture was heated overnight at 80° C. Cooled to room temperature after twenty hours, transferred to a 300 mL flask and concentrated. The residue was triturated in water and filtered to yield the title product as a brown solid (5.3 g) 1H NMR (400 MHz, CDCl3) 1.84–1.87(m, 2H), 2.72(t, J=6.2 Hz, 2H), 2.79(t, J=6.6 Hz, 2H), 3.80(s, 3H), 6.65(d, J=2.6 Hz, 1H), 6.76(dd, J=11.5, 2.7 Hz, 1H), 7.86 (d, J=8.8 Hz, 1H)

Workup

  1. temperatureCooled to room temperature after twenty hours
  2. customtransferred to a 300 mL flask
  3. concentrationconcentrated
  4. customThe residue was triturated in water
  5. filtrationfiltered

Sources & evidence

ORD record
ord-5f4436b200a24e5bba520f9b1a233df4
Source dataset
uspto-grants-2007_01
Patent number
US07169773B2

Reaction notes

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