Pyridine → 7-bromo-1-oxo-4,4,6-trimethyl-1,2,3,4-tetrahydronaphthalene-O-methyloxime

HRID 915175Notes

Reaction equation

HRID 915175 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:14])([CH3:13])[CH2:7][CH2:8][C:9]2=O)=[CH:4][C:3]=1[CH3:15].Cl.[O:17]([NH2:19])[CH3:18].N1C=CC=CC=1>C(O)C>[CH3:18][O:17][N:19]=[C:9]1[C:10]2[C:5](=[CH:4][C:3]([CH3:15])=[C:2]([Br:1])[CH:11]=2)[C:6]([CH3:14])([CH3:13])[CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 121061407-bromo-4,4,6-trimethyl-3,4-dihydro-2H-naphthalen-1-one

Product 1

HCID 865883617-bromo-1-oxo-4,4,6-trimethyl-1,2,3,4-tetrahydronaphthalene-O-methyloximeYield 99.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 7-bromo-1-oxo-4,4,6-trimethyl-1,2,3,4-tetrahydronaphthalene (1.02 g, 3.82 mmol), methoxylamine hydrochloride (0.638 mg, 7.63 mmol) and pyridine (0.93 mL, 11.46 mmol) in ethanol (30 mL) was refluxed for 3 hours. The mixture was concentrated in vacuo then diluted with water and extracted twice with ethyl acetate. The combined organic layer was dried (Mg2SO4), filtered and evaporated to give 1.13 g of 7-bromo-1-oxo-4,4,6-trimethyl-1,2,3,4-tetrahydronaphthalene-O-methyloxime as a yellow oil (quantitative) and used without further purification in the Suzuki coupling (step a). 1H NMR (300 MHz; CDCl3): 1.25 (s, 6 H), 1.75 (t, J=6.9 Hz, 2 H), 2.38 (s, 3 H), 2.73 (t, J=6.9 Hz, 2 H), 3.98 (s, 3 H), 7.17 (s, 1 H), 8.11 (s, 1 H).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additionthen diluted with water
  3. extractionextracted twice with ethyl acetate
  4. dry with materialThe combined organic layer was dried (Mg2SO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-d3cf910b7af2474d9e8ed43bce46a339
Source dataset
uspto-grants-2007_09
Patent number
US07265139B2

Reaction notes

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