HCID 20478375, compound → HCID 13543928, compound

HRID 904706Notes

Reaction equation

HRID 904706 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([CH2:22][CH2:23][CH3:24])[C:8]3[O:15][CH:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:13][C:12](=[O:21])[C:9]=3[CH:10]=2)[N:5]=[C:4]([C:25]([O:27][CH3:28])=[O:26])[CH:3]=1>C1(C(C)C)C=CC(C)=CC=1.[Pd]>[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([CH2:22][CH2:23][CH3:24])[C:8]3[O:15][C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:13][C:12](=[O:21])[C:9]=3[CH:10]=2)[N:5]=[C:4]([C:25]([O:27][CH3:28])=[O:26])[CH:3]=1

Participants

4

Reactant 1

HCID 20478375HCID 20478375, compound

Product 1

HCID 13543928HCID 13543928, compoundYield 6.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 7463P-CymeneSolvent

Procedure

Ethyl 6-chloro-2,3-dihydro-8-methoxycarbonyl-4-oxo-10-propyl-4H-pyrano[3,2-g]quinoline-2-carboxylate (0.405 g) was suspended in cymene (10 ml) and refluxed with Pd/C (5%, 0.200 g) for 10 hours. The whole was filtered hot, to remove the catalyst, cooled, poured into petroleum ether (40°-60°, 40 ml), to give a pale buff solid, which was chromatographed of silica, to give the title compound, (0.027 g) mp 174°-176°.

Workup

  1. filtrationThe whole was filtered hot
  2. customto remove the catalyst
  3. temperaturecooled
  4. additionpoured into petroleum ether (40°-60°, 40 ml)
  5. customto give a pale buff solid, which
  6. customwas chromatographed of silica

Sources & evidence

ORD record
ord-bfc7f941b54a452d8a00e7dd85e3aae9
Source dataset
uspto-grants-1983_12
Patent number
US04419352

Reaction notes

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