HCID 19000162, compound → HCID 19000165, compound

HRID 725403Notes

Reaction equation

HRID 725403 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19]CC3C=CC=CC=3)=[C:15]([O:27][CH3:28])[CH:14]=2)=[O:12])[CH:2]=1>FC(F)(F)C(O)=O>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([O:27][CH3:28])[CH:14]=2)=[O:12])[CH:2]=1

Participants

3

Reactant 1

HCID 19000162HCID 19000162, compound

Product 1

HCID 19000165HCID 19000165, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

11.0 g of 4-(benzyloxy)-3-methoxyphenyl (3-quinolinyl) ketone are treated with 50 ml of trifluoroacetic acid, whereupon the mixture is stirred at room temperature for 2 hours. After distillation of the trifluoroacetic acid, the residue is treated twice with 50 ml of ethanol each time and the solvent is distilled each time. The oil obtained crystallizes upon treatment with ethanol. After recrystallization from ethanol, there is obtained 4-hydroxy-3-methoxyphenyl (3-quinolinyl) ketone in the form of yellowish crystals of m.p. 196°-197°.

Workup

  1. distillationAfter distillation of the trifluoroacetic acid
  2. additionthe residue is treated twice with 50 ml of ethanol each time
  3. distillationthe solvent is distilled each time
  4. customThe oil obtained
  5. customcrystallizes upon treatment with ethanol
  6. customAfter recrystallization from ethanol

Sources & evidence

ORD record
ord-8e70d41915ab44b3bb231151fb0607e6
Source dataset
uspto-grants-1998_01
Patent number
US05705703

Reaction notes

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