Acetic Acid → 61001-18-1

HRID 616718Notes

Reaction equation

HRID 616718 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH:14]=[CH:13][N:12]3[CH:21]=2)=[CH:5][CH:4]=1.C(O)C.C(O)(=O)C>[Pd].[OH-].[NH4+]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH2:14][CH2:13][N:12]3[CH:21]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 702EthanolHCID 74606161001-01-2

Product 1

HCID 1315607761001-18-1

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 14923Ammonium HydroxideSolvent

Procedure

To a one liter autoclave are charged 7.1 g. of 2-(4-methoxyphenyl)imidazo[2,1-a]isoquinoline, 210 ml. of ethanol, 150 ml. of acetic acid and 0.55 g. of 10% palladium on charcoal. After flushing and filling the autoclave with hydrogen, the mixture is hydrogenated at 90° C. and 10 atmospheres for 3 hours. After absorption of 1.5 atmospheres of hydrogen gas, the autoclave is cooled and vented and 200 ml. of CHCl3 is added to the reaction mixture. The catalyst is filtered off, and the solution is evaporated to dryness, giving a solid residue which is suspended in 10% ammonium hydroxide, then extracted with dichloromethane. After drying over Na2SO4, the organic solvent is evaporated off and the residue is crystallized from ethanol giving 4.55 g. of the title product, which melts at 179°-81° C.

Workup

  1. additionTo a one liter autoclave are charged 7.1 g
  2. customAfter flushing
  3. customis hydrogenated at 90° C.
  4. customAfter absorption of 1.5 atmospheres of hydrogen gas
  5. temperaturethe autoclave is cooled
  6. additionof CHCl3 is added to the reaction mixture
  7. filtrationThe catalyst is filtered off
  8. customthe solution is evaporated to dryness
  9. customgiving a solid residue which
  10. extractionextracted with dichloromethane
  11. dry with materialAfter drying over Na2SO4
  12. customthe organic solvent is evaporated off
  13. customthe residue is crystallized from ethanol giving 4.55 g

Sources & evidence

ORD record
ord-cfdf6ad783294052bf990d6e9b5e2dcc
Source dataset
uspto-grants-1978_02
Patent number
US04075342

Reaction notes

Loading…