Formic Acid → HCID 66781369, compound

HRID 1095706Notes

Reaction equation

HRID 1095706 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%

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 (5.00 g, 11.8 mmol) was slurried in MeOH (118 ml). Ammonium formate (7.41 g, 117 mmol) and Pd(OH)2/C (0.82 g, 0.59 mmol) were added, and the reaction was heated at reflux for 2 hours. The reaction mixture was cooled to 20° C. and formic acid was added to the slurry until solids went into solution. The resulting mixture was filtered and washed with 100 ml 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 and solids were allowed to stir 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. The solids were dried under vacuum for 12 hours to obtain 3.8 g (96% yield) of the desired product.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 2 hours
  3. filtrationThe resulting mixture was filtered
  4. washwashed with 100 ml 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
  10. filtrationThe solids were collected by filtration
  11. concentrationconcentrated to dryness
  12. customThe solids were dried under vacuum for 12 hours

Sources & evidence

ORD record
ord-ab7f4bdcdabd481d99c92d5ed931882f
Source dataset
uspto-grants-2012_03
Patent number
US08138181B2

Reaction notes

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