Trifluoroacetic acid → HCID 20240299, compound

HRID 364138Notes

Reaction equation

HRID 364138 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[O:9][CH2:8][C:7](=O)[CH2:6]2.[NH:14]1C[CH2:17][CH2:16][CH2:15]1.FC(F)(F)C(O)=[O:22]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[O:9][CH2:8][C:7]3[NH:14][C:15](=[O:22])[CH2:16][CH2:17][C:6]=3[C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 31268PyrrolidineHCID 140069116-Methoxy-2H-1-benzopyran-3(4H)-one

Product 1

HCID 20240299HCID 20240299, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The starting material is prepared as follows: A solution of 17.8 g of 6-methoxy-3-chromanone, 7.5 g of pyrrolidine and 0.1 ml of trifluoroacetic acid in 200 ml of toluene is refluxed for 8 hours in a Dean Stark apparatus. After removal of solvent in vacuo 14.0 g of acrylamide is added and the mixture is heated for 3 hours at 80°. Water is added, the organic layer is separated and evaporated to dryness to afford 9-methoxy-1,2,3,5-tetrahydro-4H-[1]-benzopyrano[3,4-b]pyridin-3-one.

Workup

  1. customThe starting material is prepared
  2. customAfter removal of solvent in vacuo 14.0 g of acrylamide
  3. additionis added
  4. temperaturethe mixture is heated for 3 hours at 80°
  5. additionWater is added
  6. customthe organic layer is separated
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-bcec6d3bcd044a71a75cf4d574e9cad1
Source dataset
uspto-grants-1986_08
Patent number
US04604397

Reaction notes

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