Methanol → HCID 5483123, compound

HRID 1521573Notes

Reaction equation

HRID 1521573 reaction equation
[C:1]1(=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.Cl.[NH2:13][OH:14].C([O-])(=O)C.[Na+].CO>O>[OH:14]/[N:13]=[C:1]1\[CH2:2][CH2:3][CH2:4][C:5]2[C:10]\1=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

6

Reactant 4

HCID 887MethanolHCID 107241-TetraloneHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 5483123HCID 5483123, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 3,4-dihydro-1-(2H)-naphthalenone (72.4 g, 0.495 mol), hydroxylamine hydrochloride (139 g, 1.98 mol), sodium acetate (162 g, 1.98 mol), methanol (500 mL) and water (100 mL) was refluxed for 6 hours. The reaction mixture was diluted with water (2 L), and extracted with ether (800 mL). The organic layer was washed with water, dried and concentrated. The residue was crystallized from ether/hexane to give the title compound: LCMS m/z=162.0 [M+H]+.

Workup

  1. temperaturewas refluxed for 6 hours
  2. extractionextracted with ether (800 mL)
  3. washThe organic layer was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was crystallized from ether/hexane

Sources & evidence

ORD record
ord-785a81baeb1042d4a06ed077a2b01588
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

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