Water → HCID 67280098, compound

HRID 1692590Notes

Reaction equation

HRID 1692590 reaction equation
[CH2:1]([N:8]([CH2:19][CH2:20][OH:21])[C:9](=[O:18])[C:10]1[CH:15]=[CH:14][N+:13]([O-:16])=[CH:12][C:11]=1F)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].O>C1COCC1>[CH2:1]([N:8]1[C:9](=[O:18])[C:10]2[CH:15]=[CH:14][N+:13]([O-:16])=[CH:12][C:11]=2[O:21][CH2:20][CH2:19]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 67279753HCID 67279753, compound

Product 1

HCID 67280098HCID 67280098, compoundYield 48.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of the compound (0.60 g) obtained in step 3 in THF (15 mL) was added sodium hydride (60% in oil, 0.34 g), and the mixture was stirred at 80° C. for 4 hr. The reaction mixture was poured into water, and the resultant product was extracted three times with ethyl acetate. The organic layer was washed with brine, and concentrated. The residue was purified by silica gel column chromatography (solvent gradient; 80% ethyl acetate/hexane→5% ammonia/ethyl acetate) to give 4-benzyl-3,4-dihydropyrido[4,3-f][1,4]oxazepin-5(2H)-one 8-oxide (0.27 g, 48%) as a white powder.

Workup

  1. extractionthe resultant product was extracted three times with ethyl acetate
  2. washThe organic layer was washed with brine
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography (solvent gradient; 80% ethyl acetate/hexane→5% ammonia/ethyl acetate)

Sources & evidence

ORD record
ord-35c00752f35c4334a250137d0f8ea4fb
Source dataset
uspto-grants-2012_04
Patent number
US08158617B2

Reaction notes

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