Trifluoroacetic acid → HCID 23260547, compound

HRID 620903Notes

Reaction equation

HRID 620903 reaction equation
Cl[C:2]1[C:3]2[C:8]([C:9]([OH:23])=[C:10]3[C:19]=1[C:18](=[O:20])[C:17]1[CH2:16][C:15](=[O:21])[CH2:14][CH2:13][C:12]=1[C:11]3=[O:22])=[C:7]([OH:24])[CH:6]=[CH:5][CH:4]=2.FC(F)(F)C(O)=[O:28]>O>[OH:24][C:7]1[C:8]2[C:9](=[O:23])[C:10]3[C:19](=[C:18]([OH:20])[C:17]4[CH2:16][C:15](=[O:21])[CH2:14][CH2:13][C:12]=4[C:11]=3[OH:22])[C:2](=[O:28])[C:3]=2[CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21245414HCID 21245414, compound2×

Product 1

HCID 23260547HCID 23260547, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of ethylene acetal of 3,4-dihydro-11-chloro6,7-dihydroxy-2,5,12(1H)-naphthacenetrione (compound 11) (4 mg) in trifluoroacetic acid (2 ml) was heated at 80° under reflux for 1 h. The solution was cooled, diluted with distilled water (10 ml) and extracted with ethyl acetate. The combined organic layers were washed with distilled water, dried and evaporated to give the crude product (compound 8) which was recrystallized from ethyl acetate as brown microcrystals (2.5 mg 74%).

Workup

  1. temperatureunder reflux for 1 h
  2. temperatureThe solution was cooled
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were washed with distilled water
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-3023c31164554586bc4012db20f70443
Source dataset
uspto-grants-1989_04
Patent number
US04822873

Reaction notes

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