HCID 178418361, compound → HCID 178439523, compound

HRID 267222Notes

Reaction equation

HRID 267222 reaction equation
[CH2:1]([C:4]1[C:5]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:6][C:7]2[C:12]([C:13]=1[OH:14])=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:2]=[CH2:3].[H][H]>[Pd].C(O)C>[CH2:1]([C:4]1[C:5]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:6][C:7]2[C:12]([C:13]=1[OH:14])=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:2][CH3:3]

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178439522HCID 178439522, compound

Product 1

HCID 178439523HCID 178439523, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 49.0 parts of ethyl 3-allyl-4-hydroxy-quinoline-2-carboxylate in 600 parts of boiling ethanol was stirred for 5 minutes in 3 parts of 3% palladium-on-carbon catalyst, then filtered and the filtrate together with 5 parts of fresh catalyst was charged to a stainless steel autoclave and hydrogen added at room temperature to a pressure of 50 atmospheres. After stirring at 16 hours 1.38 moles of hydrogen had been absorbed. The reaction mixture was dissolved in hot ethanol, filtered to remove catalyst, and evaporated to give 39.3 parts of ethyl 3-n-propyl-4-hydroxyquinoline-2-carboxylate, pale yellow needles, m.pt. 155°-157°C which were collected and dried; a further 4.8 parts of less pure product m.pt. 140°-146°C were recovered from the ethanolic mother liquors after concentration in vacuo. After repeated recrystallisation from ethanol very pale yellow prismatic needles, m.pt. 158°-159.5°C were obtained. (Found: C 69.3; H 6.3; N 5.2%. C15H17NO3 requires C 69.5; H 6.6; N 5.4%).

Workup

  1. filtrationfiltered
  2. additionthe filtrate together with 5 parts of fresh catalyst was charged to a stainless steel autoclave and hydrogen
  3. additionadded at room temperature to a pressure of 50 atmospheres
  4. customhad been absorbed
  5. dissolutionThe reaction mixture was dissolved in hot ethanol
  6. filtrationfiltered
  7. customto remove catalyst
  8. customevaporated

Sources & evidence

ORD record
ord-67c6dafcd3b24580882853466a03ef56
Source dataset
uspto-grants-1976_03
Patent number
US03941793

Reaction notes

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