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

HRID 451619Notes

Reaction equation

HRID 451619 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-884712706ee14c21a8251d7c2c6f3e3d
Source dataset
uspto-grants-2013_07
Patent number
US08487116B2

Reaction notes

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