Diethyl Ether → 4-Nitro-indan-1-one O-methyl-oxime

HRID 1818023Notes

Reaction equation

HRID 1818023 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][CH2:7][C:8]2=O)([O-:3])=[O:2].Cl.[O:15]([NH2:17])[CH3:16].C(N(CC)CC)C.CCOCC>CO>[CH3:16][O:15][N:17]=[C:8]1[C:9]2[C:5](=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=[CH:11][CH:10]=2)[CH2:6][CH2:7]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 905634-Nitroindan-1-oneHCID 521874O-Methylhydroxylamine hydrochloride

Product 1

HCID 866237934-Nitro-indan-1-one O-methyl-oximeYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-nitroindane-1-one (4.75 g, 26.81 mmol) in MeOH was added methoxyl amine hydrochloride (4.50 g, 53.88 mmol) and triethyl amine (7.50 mL, 53.81 mmol). After refluxing overnight, the reaction mixture was cooled to room temperature and extracted with EtOAc (3×200 mL). The combined organic extracts were washed with H2O (3×200 mL), brine (1×200 mL), dried over MgSO4 and concentrated. Purification by column chromatography using hex: Et2O (4:1) as eluant afforded 5.31 g (97% yield) of the title compound. Spectroscopic data: 1H NMR (300 MHz, CDCl3) δ (1st isomer) 2.92-2.98 (m, 2H), 3.50-3.56 (m, 2H), 4.01 (s, 3H), 7.45 (t, J=7.62 Hz, 1H), 8.00 (d, J=7.33 Hz, 1H), 8.20 (d, J=7.92 Hz, 1H). 2nd isomer: 2.90-2.98 (m, 2H), 3.49-3.58 (m, 2H), 4.02 (s, 3H), 7.45 (t, J=8.21 Hz, 1H), 8.19 (d, J=8.21 Hz, 1H), 8.66 (d, J=7.92 Hz, 1H).

Workup

  1. temperatureAfter refluxing overnight
  2. extractionextracted with EtOAc (3×200 mL)
  3. washThe combined organic extracts were washed with H2O (3×200 mL), brine (1×200 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customPurification by column chromatography

Sources & evidence

ORD record
ord-00aaa21306fd4cc09df734c709f23795
Source dataset
uspto-grants-2009_10
Patent number
US07598417B2

Reaction notes

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