Ethanol → HCID 20368788, compound

HRID 616720Notes

Reaction equation

HRID 616720 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[N:10]=[C:11]3[CH:20]=[CH:19][C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[N:12]3[CH:21]=2)[CH:6]=[CH:7][CH:8]=1.C(O)C>[Pd].C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[N:10]=[C:11]3[CH2:20][CH2:19][C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[N:12]3[CH:21]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 20368783HCID 20368783, compound

Product 1

HCID 20368788HCID 20368788, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

2-(3-Methoxyphenyl)imidazo[1,2-a]quinoline (2.74 g) together with 0.5 g. of 10% palladium on charcoal, 35 ml. of ethanol and 25 ml. of acetic acid is hydrogenated at 90° C. and 10 atmospheres for five hours. After filtration of the catalyst, the solution is evaporated to dryness and the residue is washed with water and aqueous solution carbonate. The resulting solid is extracted with ethyl ether and the organic solution, after drying, is evaporated to yield a product which, after crystallization from a hexane dichloromethane mixture, melts at 107°-9° C.

Workup

  1. customis hydrogenated at 90° C.
  2. filtrationAfter filtration of the catalyst
  3. customthe solution is evaporated to dryness
  4. washthe residue is washed with water and aqueous solution carbonate
  5. extractionThe resulting solid is extracted with ethyl ether
  6. customthe organic solution, after drying
  7. customis evaporated
  8. customto yield a product which
  9. customafter crystallization from a hexane dichloromethane mixture, melts at 107°-9° C.

Sources & evidence

ORD record
ord-8595ebe14ce6468f89c82926164d88c5
Source dataset
uspto-grants-1978_02
Patent number
US04075342

Reaction notes

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