Trifluoroacetic acid → HCID 20154005, compound

HRID 364122Notes

Reaction equation

HRID 364122 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH2:10][C:9](=O)[CH2:8][C:7]=2[CH:13]=1.[CH2:14]([NH:17][CH2:18][CH2:19][C:20](OC)=[O:21])[CH2:15][CH3:16].FC(F)(F)C(O)=O>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH2:10][C:9]3[N:17]([CH2:14][CH2:15][CH3:16])[CH2:18][CH2:19][C:20](=[O:21])[C:8]=3[C:7]=2[CH:13]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acid2×HCID 10630640HCID 10630640, compoundHCID 140069116-Methoxy-2H-1-benzopyran-3(4H)-one

Product 1

HCID 20154005HCID 20154005, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 8.9 g of 6-methoxy-2H-[1]-benzopyran-3-one, 7.46 g of methyl 3-(propylamino)-propionate, 0.8 ml of trifluoroacetic acid in 80 ml toluene is refluxed for 7 hours in a Dean Stark apparatus; additional 0.8 ml portions of trifluoroacetic acid are added at 2, 4 and 6 hours. The reaction mixture is cooled and the solvent is removed in vacuo. The residue is crystallized from ether/methanol to afford 9-methoxy-4-propyl-1,2,3,5-tetrahydro-4H-[1]-benzopyrano[3,4-b]pyridin-1-one, m.p. 97°-100°.

Workup

  1. temperatureis refluxed for 7 hours in a Dean Stark apparatus
  2. temperatureThe reaction mixture is cooled
  3. customthe solvent is removed in vacuo
  4. customThe residue is crystallized from ether/methanol

Sources & evidence

ORD record
ord-6a2e0d0a6c714184a3b013d18cb319d6
Source dataset
uspto-grants-1986_08
Patent number
US04604397

Reaction notes

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