Formic Acid → HCID 66781369, compound

HRID 1095724Notes

Reaction equation

HRID 1095724 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16]([C:19]1[N:23]3[CH:24]=[CH:25][C:26]([O:28][CH2:29][CH2:30][O:31][CH3:32])=[CH:27][C:22]3=[N:21][CH:20]=1)[CH:15]=[CH:14]2)C1C=CC=CC=1.C([O-])=O.[NH4+].C(O)=O>CO.[OH-].[OH-].[Pd+2]>[CH3:32][O:31][CH2:30][CH2:29][O:28][C:26]1[CH:25]=[CH:24][N:23]2[C:19]([C:16]3[CH:15]=[CH:14][C:13]4[C:18](=[C:9]([OH:8])[CH:10]=[CH:11][CH:12]=4)[N:17]=3)=[CH:20][N:21]=[C:22]2[CH:27]=1

Participants

6

Reactant 3

HCID 284Formic AcidHCID 2723923Ammonium formateHCID 667814488-(Benzyloxy)-2-(7-(2-methoxyethoxy)-imidazo[1,2-a]pyridin-3-yl)quinoline

Product 1

HCID 66781369HCID 66781369, compoundYield 96.4%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

8-(Benzyloxy)-2-(7-(2-methoxyethoxy)-imidazo[1,2-a]pyridin-3-yl)quinoline (5.0 g, 11.75 mmol) was slurried in MeOH (117.5 ml). Ammonium formate (7.410 g, 117.5 mmol) and Pd(OH)2/C (0.8252 g, 0.5876 mmol) were added. The reaction mixture was heated to reflux for 2 hours, then cooled to 20° C. Formic acid was added to the slurry until solids went into solution. The mixture was filtered and the filter paper was washed with 10% formic acid in methanol. The filtrate was concentrated to an oil. To the oil was added an excess of NH3 in methanol and resulting the solids were concentrated to dryness. Water was added to the solids and the slurry was stirred for 1 hour (pH was 6.5-7.0 by pH paper). The solids were collected by filtration and then taken up in toluene and concentrated to dryness under vacuum dry for 12 hours to obtain 3.8 g (96% yield) of the desired product.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 2 hours
  3. filtrationThe mixture was filtered
  4. washthe filter paper was washed with 10% formic acid in methanol
  5. concentrationThe filtrate was concentrated to an oil
  6. additionTo the oil was added an excess of NH3 in methanol
  7. customresulting the solids
  8. concentrationwere concentrated to dryness
  9. additionWater was added to the solids
  10. filtrationThe solids were collected by filtration
  11. concentrationconcentrated to dryness under vacuum
  12. customdry for 12 hours

Sources & evidence

ORD record
ord-f7c9ceb917d04449b778c78967a5193d
Source dataset
uspto-grants-2012_03
Patent number
US08138181B2

Reaction notes

Loading…