Potassium Carbonate → HCID 15712183, compound

HRID 1012559Notes

Reaction equation

HRID 1012559 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.I[C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>[Cu].CN(C)C=O>[C:15]1([CH3:18])[CH:16]=[CH:17][C:12]([N:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH2:4][CH2:3][CH2:2]2)=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 122074-IodotolueneHCID 694601,2,3,4-Tetrahydroquinoline

Product 1

HCID 15712183HCID 15712183, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6228DimethylformamideSolvent

Procedure

Under the atmosphere of nitrogen, 4 parts of 1,2,3,4-tetrahydroquinoline, 20 parts of 4-iodotoluene, 20 parts of dimethylformamide (DMF), 10 parts of potassium carbonate, and 1 part of copper powder (200 mesh) were stirred at 160° C. for 10 hours. After the reaction, the resultant was extracted with water/ethyl acetate, and the ethyl acetate phase was dried over magnesium sulfate. Ethyl acetate was distilled off, and the residue was separated and purified by column chromatography to yield 5 parts of a precursor of the compound (303), 1,2,3,4-tetrahydro-1-p-tolylquinoline as a colorless crystal. Next, 1.7 parts of phosphorus oxychloride were dropwise added to 10 parts of chloroform and 1 part of N,N-dimethylacrolein, the temperature of which was adjusted to 5° C., while the temperature of the reaction solution was kept at 10° C. or lower. The reaction solution was then stirred at 5° C. for 1 hour. Thereafter, 2.0 parts of 1,2,3,4-tetrahydro-1-p-tolylquinoline described above were added thereto, and then the reactive components were caused to react at 25° C. for 1 hour. The reaction solution was then stirred at 70° C. for 1 hour. Thereafter, a 20% solution of sodium hydroxide in water was added to the reaction solution until the pH turned to 12. The precipitated crystal was filtrated, and the resultant crystal was washed with water. The crystal was then separated by column chromatography (hexane/ethyl acetate), and recrystallized from ethanol to yield 1.8 parts of the compound (303) as a yellow crystal.

Workup

  1. customAfter the reaction
  2. extractionthe resultant was extracted with water/ethyl acetate
  3. dry with materialthe ethyl acetate phase was dried over magnesium sulfate
  4. distillationEthyl acetate was distilled off
  5. customthe residue was separated
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-792833655a284ef98f92621548d6c672
Source dataset
uspto-grants-2011_07
Patent number
US07977570B2

Reaction notes

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