HCID 20081816, compound → HCID 9878343, compound

HRID 1681248Notes

Reaction equation

HRID 1681248 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:19])=[CH:5][CH:6]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[C:7]=1[C:8]([O:10][CH3:11])=[O:9]>C(O)(=O)C.[O-2].[Cr+6].[O-2].[O-2]>[CH3:1][C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH:5]=[C:4]([CH3:19])[N:3]=1

Participants

4

Reactant 1

HCID 20081816HCID 20081816, compound

Product 1

HCID 9878343HCID 9878343, compound

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 176Acetic AcidSolvent

Procedure

8.6 g (33 mmol) of crude product from Example 27 and 3.3 g of chromium (VI) oxide are heated under reflux for 1 hour in 90 ml of glacial acetic acid. The solvent is then removed on the rotary evaporator, ethyl acetate/petroleum ether 1:1 is added to the residue and undissolved material is filtered off with suction. The mother liquor is concentrated in vacuo and chromatographed over 500 g of silica gel using ethyl acetate/petroleum ether 1:1.

Workup

  1. customThe solvent is then removed on the rotary evaporator, ethyl acetate/petroleum ether 1:1
  2. additionis added to the residue and undissolved material
  3. filtrationis filtered off with suction
  4. concentrationThe mother liquor is concentrated in vacuo
  5. customchromatographed over 500 g of silica gel

Sources & evidence

ORD record
ord-51149787fd404db0b6c3ef88a88d96b0
Source dataset
uspto-grants-1992_12
Patent number
US05169857

Reaction notes

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