Formic Acid → HCID 18439913, compound

HRID 1394124Notes

Reaction equation

HRID 1394124 reaction equation
[CH:1](O)=[O:2].[C:4]([O:7][C:8](=[O:10])C)(=[O:6])C.[CH3:11][O:12][C:13]1[CH:14]=[C:15]([C:19]2[CH:28]=[C:27]([NH2:29])[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([NH2:30])[CH:25]=3)[N:20]=2)[CH:16]=[CH:17][CH:18]=1.CCOCC>C1COCC1>[CH:4]([O:7][CH:8]=[O:10])=[O:6].[NH2:29][C:27]1[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([NH:30][CH:1]=[O:2])[CH:25]=2)[N:20]=[C:19]([C:15]2[CH:16]=[CH:17][CH:18]=[C:13]([O:12][CH3:11])[CH:14]=2)[CH:28]=1

Participants

7

Reactant 4

HCID 284Formic AcidHCID 3283Diethyl EtherHCID 7918Acetic AnhydrideHCID 18439888HCID 18439888, compound

Product 2

HCID 9548680Formic anhydrideHCID 18439913HCID 18439913, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

Formic anhydride was prepared by placing 260 mg (5.66 mmoles) of formic acid into a dry 100 mL round-bottom flask equipped with a condenser, magnetic stirrer and a nitrogen inlet. The flask was cooled with an ice bath and then 470 mg (4.61 mmoles) of acetic anhydride was added. The stirring solution was then gently warmed to 50° C. with an oil bath for 2 hrs. After this time the reaction was cooled, and 25 mL of dry THF was added followed by the addition of 1.0 g (3.77 mmoles) of 2-(3-methoxyphenyl)-4,6-quinolinediamine as a solution in 10 mL of dry THF. The mixture was then heated to reflux for 2 hrs. At the end of this time the reaction was cooled and ether was added. The solids which formed were then collected by filtration and washed with ether. The solids were then dissolved in ethyl acetate and 5% NaOH solution, the layers separated and the organic layer dried over Na2SO4, filtered and concentrated to give 830 mg (75%) of the desired product. This product was used without further purification.

Workup

  1. customequipped with a condenser, magnetic stirrer and a nitrogen inlet
  2. temperatureThe flask was cooled with an ice bath
  3. temperatureAfter this time the reaction was cooled
  4. temperatureThe mixture was then heated
  5. temperatureto reflux for 2 hrs
  6. temperatureAt the end of this time the reaction was cooled
  7. customThe solids which formed
  8. filtrationwere then collected by filtration
  9. washwashed with ether
  10. dissolutionThe solids were then dissolved in ethyl acetate
  11. custom5% NaOH solution, the layers separated
  12. dry with materialthe organic layer dried over Na2SO4
  13. filtrationfiltered
  14. concentrationconcentrated

Sources & evidence

ORD record
ord-c5db484ba7234a54a043a25ed965ebe9
Source dataset
uspto-grants-2008_03
Patent number
US07348340B2

Reaction notes

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