Potassium Hydroxide → HCID 11964486, compound

HRID 1170948Notes

Reaction equation

HRID 1170948 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:17])[C:7]3[C:12]([NH:13][C:14]=2[CH:15]=1)=[CH:11][C:10]([Cl:16])=[CH:9][CH:8]=3.[OH-].[K+].Br[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([F:29])([F:28])[F:27]>CO>[F:27][C:26]([F:29])([F:28])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][O:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:17])[C:7]3[C:12]([NH:13][C:14]=2[CH:15]=1)=[CH:11][C:10]([Cl:16])=[CH:9][CH:8]=3

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 138454716-Bromo-1,1,1-trifluorohexaneHCID 68712477HCID 68712477, compound

Product 1

HCID 11964486HCID 11964486, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

3-hydroxy-6-chloroacridone (594 mg) was stirred in 10 ml of methanol, and 5 ml of methanolic KOH (30 mg/ml) was added (1 equiv. base), whereupon complete dissolution occurred. 1-Bromo-5-trifluoromethylpentane (2.03 g, 3 equiv.) was added and the solution heated at 70° C. overnight, forming a fine solid precipitate; after cooling, 0.35 g of pale yellow powder was collected by filtration. When the filtrate is heated another 2 days, the same quantity of product may be isolated in addition. The crude product was crystallized from methanol. Analogous procedures can be applied for preparation of compounds with the O(CH2)3CF3, O(CH2)4CF3, O(CH2)7CF3, and O(CH2)10CF3— side chains and including aromatic ketone derivatives bearing O(CH2)C2F5 and O(CH2)C3F7 side chains.

Workup

  1. dissolutionwhereupon complete dissolution
  2. customforming a fine solid precipitate
  3. temperatureafter cooling
  4. filtration0.35 g of pale yellow powder was collected by filtration
  5. temperatureWhen the filtrate is heated another 2 days
  6. customthe same quantity of product may be isolated in addition
  7. customThe crude product was crystallized from methanol
  8. customAnalogous procedures can be applied for preparation of compounds with the O(CH2)3CF3, O(CH2)4CF3, O(CH2)7CF3, and O(CH2)10CF3— side chains

Sources & evidence

ORD record
ord-c1856e012c564a0e9005aaad1199317e
Source dataset
uspto-grants-2010_11
Patent number
US07829578B1

Reaction notes

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