2-Cyclohexylacetaldehyde → 3-Cyclohexyl-quinoline-5-carboxylic acid

HRID 1779953Notes

Reaction equation

HRID 1779953 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6](O)[O:7][C:8]2=[O:9])([O-])=O.[CH:15]1([CH2:21][CH:22]=O)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.C[O-].[Na+]>C(O)(C)C.[Pd].S([O-])([O-])(=O)=O.[Ba+2]>[CH:15]1([C:21]2[CH:22]=[N:1][C:4]3[CH:13]=[CH:12][CH:11]=[C:10]([C:8]([OH:7])=[O:9])[C:5]=3[CH:6]=2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

6

Reactant 3

HCID 3166272-CyclohexylacetaldehydeHCID 10942334Sodium MethoxideHCID 110955283-hydroxy-4-nitro-3H-isobenzofuran-1-one

Product 1

HCID 190487293-Cyclohexyl-quinoline-5-carboxylic acid

Reagents, catalysts & solvents 2

HCID 16218511Pd barium sulfateCatalystHCID 3776IsopropanolSolvent

Procedure

A mixture of 50 g of 4-nitro-3-hydroxyphthalide in 200 ml of isopropanol is hydrogenated with 5 g of Pd/barium sulphate under 3.5 bar, during which the temperature rises to 55° C. When the hydrogenation has ended (about 30 minutes), the catalyst is filtered off hot with suction. 33 g (260 mmol) of cyclohexylacetaldehyde are added to the filtrate and, after addition of a catalytic amount of sodium methylate, the mixture is heated under reflux for 20 hours. After cooling, the crystals which have precipitated out are filtered off with suction and washed with isopropanol. 15 g of virtually colourless product with a melting point of over 280° C. are obtained.

Workup

  1. customrises to 55° C
  2. custom(about 30 minutes)
  3. filtrationthe catalyst is filtered off hot with suction
  4. temperaturethe mixture is heated
  5. temperatureunder reflux for 20 hours
  6. temperatureAfter cooling
  7. customthe crystals which have precipitated out
  8. filtrationare filtered off with suction
  9. washwashed with isopropanol
  10. custom15 g of virtually colourless product with a melting point of over 280° C. are obtained

Sources & evidence

ORD record
ord-4c55477ba29840a5ab0901dee533f253
Source dataset
uspto-grants-1997_05
Patent number
US05629320

Reaction notes

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