HCID 19000162, compound → HCID 19000165, compound

HRID 274535Notes

Reaction equation

HRID 274535 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-6384421b23e14d43ac50c6e3b570a479
Source dataset
uspto-grants-1995_02
Patent number
US05389653

Reaction notes

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