Phenol → HCID 68429387, compound

HRID 2191292Notes

Reaction equation

HRID 2191292 reaction equation
[CH2:1]([N:8]1[C:14](=[O:15])[C:13]2[CH:16]=[CH:17][C:18](F)=[N:19][C:12]=2[O:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21]1([OH:27])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[CH2:1]([N:8]1[C:14](=[O:15])[C:13]2[CH:16]=[CH:17][C:18]([O:27][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[N:19][C:12]=2[O:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 996PhenolHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 59568636HCID 59568636, compound

Product 1

HCID 68429387HCID 68429387, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of the compound obtained in step 1 (0.50 g), phenol (0.21 g), potassium carbonate (0.76 g) and DMF (5 mL) was stirred at 100° C. for 3 days. The reaction solution was poured into water, and the resulting product was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried, and the solvent was evaporated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to give 4-benzyl-8-phenoxy-3,4-dihydropyrido[3,2-f][1,4]oxazepin-5(2H)-one (0.42 g, 66%) as a white powder.

Workup

  1. extractionthe resulting product was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-93dd9cd45ee947d0a3db505eaa37ce49
Source dataset
uspto-grants-2012_12
Patent number
US08329687B2

Reaction notes

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