Triethylamine → HCID 178425694, compound

HRID 1385032Notes

Reaction equation

HRID 1385032 reaction equation
[CH3:1][C:2]1[C:11]2[N:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]([C:12](Cl)=[O:13])=[CH:4][CH:3]=1.[OH:15][C:16]1[N:20]([CH3:21])[N:19]=[CH:18][CH:17]=1.C(N(CC)CC)C>C(#N)C.C(OCC)(=O)C>[OH:15][C:16]1[N:20]([CH3:21])[N:19]=[CH:18][C:17]=1[C:12]([C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[C:11]2[C:6]=1[CH:7]=[CH:8][CH:9]=[N:10]2)=[O:13]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 211841228-Methylquinoline-5-carbonyl chlorideHCID 178481816HCID 178481816, compound

Product 1

HCID 178425694HCID 178425694, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

At 0° C., 1.70 g of 8-methylquinoline-5-carbonyl chloride were added to 0.81 g of 5-hydroxy-1-methylpyrazole and 0.92 g of triethylamine in 30 ml of acetonitrile. The reaction mixture was stirred for 3 hours at room temperature and then taken up in ethyl acetate and washed with aqueous sodium carbonate solution, and the organic phase was then dried and concentrated. The residue was treated with 10 ml of dioxane and 1.71 g of dry potassium carbonate and heated under reflux for 14 hours. After cooling, water was added and the aqueous phase was washed with ethyl acetate and acidified with 2N hydrochloric acid. The precipitate was filtered off under suction and the acidified aqueous phase was extracted with ethyl acetate. This organic phase was dried and concentrated. The residue and the precipitate were combined.

Workup

  1. washwashed with aqueous sodium carbonate solution
  2. customthe organic phase was then dried
  3. concentrationconcentrated
  4. additionThe residue was treated with 10 ml of dioxane and 1.71 g of dry potassium carbonate
  5. temperatureheated
  6. temperatureunder reflux for 14 hours
  7. temperatureAfter cooling
  8. additionwater was added
  9. washthe aqueous phase was washed with ethyl acetate
  10. filtrationThe precipitate was filtered off under suction
  11. extractionthe acidified aqueous phase was extracted with ethyl acetate
  12. customThis organic phase was dried
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-43d12c26b9c84cedbcc07d16a08d1be7
Source dataset
uspto-grants-2001_07
Patent number
US06262074B1

Reaction notes

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