Ethanol → HCID 21293763, compound

HRID 620814Notes

Reaction equation

HRID 620814 reaction equation
[C:1](=[N:16][OH:17])([C:3]1[CH:4]=[CH:5][C:6]2[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[O:8][C:7]=2[CH:15]=1)[CH3:2].[CH2:18]([OH:20])[CH3:19].Cl.NO>N1C=CC=CC=1>[OH:17][N:16]([CH:1]([C:3]1[CH:4]=[CH:5][C:6]2[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[O:8][C:7]=2[CH:15]=1)[CH3:2])[C:18](=[O:20])[CH3:19]

Participants

5

Reactant 3

HCID 702EthanolHCID 443297Hydroxyamine hydrochlorideHCID 86742939HCID 86742939, compound

Product 1

HCID 21293763HCID 21293763, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-Acetyldibenzofuran oxime. The crude ketone prepared as described in step a, was dissolved in pyridine (50 mL) and ethanol (50 mL) and hydroxylamine hydrochloride was added. The mixture was stirred overnight at ambient temperature. The reaction was concentrated and the residue was partitioned between ethyl acetate (300 mL) and 3N HCl. The ethyl acetate layer was dried (Na2SO4), filtered and concentrated in vacuo to give a crystalline residue. The crystals were rinsed with hexane, filtered and dried to give 12.3 g of the desired product, mp 132°-135°.

Workup

  1. concentrationThe reaction was concentrated
  2. customthe residue was partitioned between ethyl acetate (300 mL) and 3N HCl
  3. dry with materialThe ethyl acetate layer was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a crystalline residue
  7. washThe crystals were rinsed with hexane
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-a9a18e0372a74963a119d0465cf71098
Source dataset
uspto-grants-1989_04
Patent number
US04822811

Reaction notes

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