1-Indanone, 4-bromo- → 4-Bromoindan-1-one O-methyloxime

HRID 656451Notes

Reaction equation

HRID 656451 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=O.Cl.[CH3:13][O:14][NH2:15]>N1C=CC=CC=1>[CH3:13][O:14][N:15]=[C:6]1[C:7]2[C:3](=[C:2]([Br:1])[CH:10]=[CH:9][CH:8]=2)[CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 987131-Indanone, 4-bromo-HCID 521874O-Methylhydroxylamine hydrochloride

Product 1

HCID 766564474-Bromoindan-1-one O-methyloxime

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-Bromoindan-1-one (5.08 g, 24.1 mmol) was added to a mixture of methoxyamine hydrochloride (2.21 g, 26.5 mmol) in pyridine (40 mL) under nitrogen atmosphere and stirred overnight at ambient temperature. The reaction mixture was concentrated, added ethyl acetate (200 mL), washed with 3N hydrochloric acid (200 mL), dried with brine and anhydrous sodium sulfate, and concentrated. Obtained 4-bromoindan-1-one O-methyloxime (5.66 g, 98%) as an orange liquid. MS (DCI/NH3) m/z: 239.94 [M+H]+. 1H NMR (DMSO-d6) □: 2.83 (m, 2H), 2.96 (m, 2H), 3.91 (s, 3H), 7.25 (t, 1H), 7.56 (d, 1H), 7.60 (d, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionadded ethyl acetate (200 mL)
  3. washwashed with 3N hydrochloric acid (200 mL)
  4. dry with materialdried with brine and anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-cec9473b9a674e208ae9ac53f7575116
Source dataset
uspto-grants-2011_12
Patent number
US08071762B2

Reaction notes

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