Pyridine → HCID 22935750, compound

HRID 1352505Notes

Reaction equation

HRID 1352505 reaction equation
C(OC(=O)C)(=[O:3])C.C1(N[C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=[CH:14][CH:13]=2)CC1.[N:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[CH:25]1([CH:26]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=[CH:14][CH:13]=2)[C:27]([NH2:22])=[O:3])[CH2:23][CH2:24]1

Participants

4

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 22935736681828-34-2

Product 1

HCID 22935750HCID 22935750, compoundYield 98.7%

Procedure

Acetic anhydride (18.3 g) was added to a solution of cyclopropyl-quinolin-4-yl-amine (6.6 g) in pyridine (50 ml) and the mixture was heated under reflux over night. After cooling, the solvent was removed under reduce pressure and then the mixture was washed with dichloromethane (200 ml) and an aqueous solution of sodium carbonate (200 ml). The organic layer was separated and dried over sodium sulfate. The solvent was removed under reduce pressure and the crude compound was purified by flash chromatography on silicagel using dichloromethane/methanol (98/2) as eluent to give cyclopropyl-quinolin-4-yl-acetamide (8 g, 98.7% yield).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux over night
  3. temperatureAfter cooling
  4. customthe solvent was removed
  5. washthe mixture was washed with dichloromethane (200 ml)
  6. customThe organic layer was separated
  7. dry with materialdried over sodium sulfate
  8. customThe solvent was removed
  9. customthe crude compound was purified by flash chromatography on silicagel

Sources & evidence

ORD record
ord-89eb4b1c909f4499bbe1ad59f0cace37
Source dataset
uspto-grants-2007_05
Patent number
US07220760B2

Reaction notes

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