Triethylamine → N-(3,4-dihydro-2H-naphthalen-1-ylidene)hydroxylamine

HRID 661630Notes

Reaction equation

HRID 661630 reaction equation
[CH2:1]1[CH2:11][C:9](=O)[C:8]2[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:2]1.Cl.[NH2:13][OH:14].C(N(CC)CC)C>CO>[C:9]1(=[N:13][OH:14])[C:8]2[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:2][CH2:1][CH2:11]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 107241-TetraloneHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 76876N-(3,4-dihydro-2H-naphthalen-1-ylidene)hydroxylamineYield 108.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of α-tetralone (10 g, 68.5 mmol) in anhydrous MeOH (175 mL), hydroxylamine hydrochloride (7.6 g, 109.6 mmol) and triethylamine (15.3 mL, 109.6 mmol) were added. The mixture was stirred at room temperature for 16 hrs, followed by removal of the solvent in vacuo. The residue was dissolved in DCM, washed with water and brine, dried (Na2SO4), filtered and concentrated in vacuo to yield crude 3,4-dihydro-2H-naphthalen-1-one oxime (12 g). MS [M+H]+: 162.1; tR=2.03 min. (method 1)

Workup

  1. customfollowed by removal of the solvent in vacuo
  2. dissolutionThe residue was dissolved in DCM
  3. washwashed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1387bc7d6b674bc8aa50217c4c28cd7d
Source dataset
uspto-grants-2011_12
Patent number
US08084614B2

Reaction notes

Loading…