Sodium Hydroxide → HCID 10659340, compound

HRID 1736707Notes

Reaction equation

HRID 1736707 reaction equation
[H-].[Al+3].[H-].[H-].[F:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:13]=[CH:14][N:15]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[NH:18][C:17](=O)[C:16]=23)=[CH:8][CH:7]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>CO>[F:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[N:13]=[CH:14][N:15]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[NH:18][CH2:17][C:16]=23)=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 21584524AluminiumhydrideHCID 56611798HCID 56611798, compound

Product 1

HCID 10659340HCID 10659340, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Aluminum hydride (0.6M in THF, 80 ml) is added to 3-(4-fluorophenyl)-4,5-dihydroimidazo[1,5-a]quinoxalin-4-one (XXXV, EXAMPLE 246, 3.21 g) and the resulting solution is heated at reflux for 36 hr. After 24 hr, lithium aluminum hydride (600 mg) is added as starting material is still present. After cooling to 20°-25°, methanol (12.1 ml) and sodium hydroxide (6N, 50.0 ml) are added successively and the resultant solution stirred for 30 min at 20°-25°. Aqueous workup (ethyl acetate, magnesium sulfate) and purification by flash chromatography eluting with hexane/ethyl acetate (2/1), pooling the appropriate fractions and concentration gives the title compound, IR (mineral oil) 3381, 2924, 1511, 1492, 1290, 1231, 838 and 741 cm-1 : NMR (CDCl3) 8.04, 7.58, 7.42, 7.0-7.2, 6.8-6.95, 4.66 and 4.07 δ; MS (m/z) 265, 264, 237, 144 and 118.

Workup

  1. temperaturethe resulting solution is heated
  2. temperatureat reflux for 36 hr
  3. temperatureAfter cooling to 20°-25°
  4. customAqueous workup (ethyl acetate, magnesium sulfate) and purification by flash chromatography
  5. washeluting with hexane/ethyl acetate (2/1)
  6. concentrationthe appropriate fractions and concentration

Sources & evidence

ORD record
ord-666e4532aed941d19449ce0c3eb6b1c3
Source dataset
uspto-grants-1996_07
Patent number
US05541324

Reaction notes

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