Hydrochloric Acid → HCID 21939851, compound

HRID 1242909Notes

Reaction equation

HRID 1242909 reaction equation
Cl.[C:2]([NH:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[CH2:12][C:11](=[O:16])[CH2:10][CH2:9]2)(=[O:4])[CH3:3].[C:17]1([C:26]2[CH:31]=[CH:30]C=[CH:28][CH:27]=2)[CH:22]=[CH:21][C:20](C(Cl)=O)=[CH:19][CH:18]=1.C(N(CC)CC)C>C(OCC)(=O)C.CN(C)C=O>[O:16]=[C:11]1[CH2:10][CH2:9][C:8]2[CH:7]=[C:6]([NH:5][C:2]([C:3]3[CH:28]=[CH:27][C:26]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)=[CH:31][CH:30]=3)=[O:4])[CH:15]=[CH:14][C:13]=2[CH2:12]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 841514-Phenylbenzoyl chlorideHCID 21939739HCID 21939739, compound

Product 1

HCID 21939851HCID 21939851, compoundYield 29.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

Concentrated hydrochloric acid (1.5 ml) was added to 6-acetamido-2-tetralone (20 mg. 0.098 mmol) obtained in Reference Example 71, which was stirred at 100° C. for 1 hour, and the solvent was distilled out under reduced pressure. Ethyl acetate was added to the residue, which was washed with aqueous potassium carbonate solution and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then the solvent was distilled out under reduced pressure. [1,1′-Biphenyl]-4-carbonyl chloride (21.3 mg, 0.098 mmol) was added to a dimethylformamide solution (0.5 ml) of the obtained oily substance and triethylamine (0.014 ml, 0.098 mmol) under ice-cooling, which was stirred at room temperature for 1 hour. Ethyl acetate was added to the reaction mixture, which was washed with 1N hydrochloric acid, aqueous potassium carbonate solution and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then the solvent was distilled out under reduced pressure. The resulting residue was purified by silica gel column chromatography (development solvent; hexane:ethyl acetate=1:1), to give the titled compound (10 mg).

Workup

  1. customobtained in Reference Example 71, which
  2. distillationthe solvent was distilled out under reduced pressure
  3. additionEthyl acetate was added to the residue, which
  4. washwas washed with aqueous potassium carbonate solution and saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled out under reduced pressure
  7. temperaturecooling
  8. stirringwhich was stirred at room temperature for 1 hour
  9. washwas washed with 1N hydrochloric acid, aqueous potassium carbonate solution and saturated aqueous sodium chloride solution
  10. dry with materialdried over anhydrous sodium sulfate
  11. distillationthe solvent was distilled out under reduced pressure
  12. customThe resulting residue was purified by silica gel column chromatography (development solvent; hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-56bd9fa2942b44f685aa870606e2754f
Source dataset
uspto-grants-2006_10
Patent number
US07115750B1

Reaction notes

Loading…