Potassium Hydroxide → HCID 23369683, compound

HRID 1900728Notes

Reaction equation

HRID 1900728 reaction equation
C([NH:4][CH2:5][C:6]1[O:20][C:9]2=[C:10]3[C:15](=[C:16]([CH3:18])[CH:17]=[C:8]2[CH:7]=1)[NH:14][C:13](=[O:19])[CH:12]=[CH:11]3)(=O)C.[OH-].[K+]>CO.O>[NH2:4][CH2:5][C:6]1[O:20][C:9]2=[C:10]3[C:15](=[C:16]([CH3:18])[CH:17]=[C:8]2[CH:7]=1)[NH:14][C:13](=[O:19])[CH:12]=[CH:11]3

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 23369702HCID 23369702, compound

Product 1

HCID 23369683HCID 23369683, compoundYield 76.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

2-(N-Acetylaminomethyl)-6,7-dihydro-5-methylfuro[2,3-f]quinoline-7-one (475 mg) was suspended in methanol (4 mg), to which KOH (1.16 g) in water (1 ml) was added. The mixture was stirred at 90° C. for 11 hours. After completion of the reaction, the solvent was removed under reduced pressure, and water (50 ml) was added. The resulting mixture was made into acidic with 2N-HCl. The aqueous phase was washed with chloroform. Potassium carbonate was added thereto up to definite alkaline pH, followed by extraction with chloroform. The chloroform phase was washed with aqueous NaCl solution, and dried. After the solvent was removed under reduced pressure, 306 mg of 2-aminomethyl-6,7-dihydro-5-methylfuro[2,3-f]quinoline-7-one (76.3%) was obtained. This product was converted into a hydrochloride, and recrystallized from methanol. As a result, a hydrochloric acid salt of 2-aminomethyl-6,7-dihydro-5-methylfuro[2,3-f]quinoline-7-one was obtained as pale yellow prisms (mp.: higher than 300° C.).

Workup

  1. additionwas added
  2. customAfter completion of the reaction
  3. customthe solvent was removed under reduced pressure, and water (50 ml)
  4. additionwas added
  5. washThe aqueous phase was washed with chloroform
  6. additionPotassium carbonate was added
  7. extractionup to definite alkaline pH, followed by extraction with chloroform
  8. washThe chloroform phase was washed with aqueous NaCl solution
  9. customdried
  10. customAfter the solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-62607a5901cf4309bbeb589f2d22e594
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

Loading…