Hydroxyamine hydrochloride → (1E)-11-(3-fluorophenyl)-1-hydroxyimino-9-methoxy-3,4-dihydro-2H-benzo[b]quinolizin-6-one

HRID 2196379Notes

Reaction equation

HRID 2196379 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[CH:16]=[C:15]([O:18][CH3:19])[CH:14]=[CH:13][C:12]=3[C:11](=[O:20])[N:10]3[CH2:21][CH2:22][CH2:23][C:24](=O)[C:9]=23)[CH:5]=[CH:6][CH:7]=1.Cl.[NH2:27][OH:28]>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[CH:16]=[C:15]([O:18][CH3:19])[CH:14]=[CH:13][C:12]=3[C:11](=[O:20])[N:10]3[CH2:21][CH2:22][CH2:23]/[C:24](=[N:27]\[OH:28])/[C:9]=23)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 1137112611-(3-fluorophenyl)-9-methoxy-3,4-dihydro-2H-pyrido[1,2-b]isoquinoline-1,6-dione

Product 1

HCID 11337105(1E)-11-(3-fluorophenyl)-1-hydroxyimino-9-methoxy-3,4-dihydro-2H-benzo[b]quinolizin-6-one

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 11-(3-fluorophenyl)-9-methoxy-3,4-dihydro-2H-pyrido[1,2-b]isoquinoline-1,6-dione (125 mg) in 4 mL pyridine was added hydroxylamine hydrochloride (51 mg). The reaction was heated to reflux for 5 h, then cooled to room temp and partitioned between ether and water. The aqueous solution was extracted with ether (2×). The combined organic solutions were washed with 1 N HCl (1×), and 10% bicarb (1×), then dried (MgSO4) and concentrated. Flash chromatography (10-70% EtOAc/hexanes) gave the titled compound.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 5 h
  3. custompartitioned between ether and water
  4. extractionThe aqueous solution was extracted with ether (2×)
  5. washThe combined organic solutions were washed with 1 N HCl (1×), and 10% bicarb (1×)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-686e6224cab74edfacaf9fbabe391def
Source dataset
uspto-grants-2012_12
Patent number
US08338449B2

Reaction notes

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