Hydrochloric Acid → HCID 67770865, compound

HRID 1900744Notes

Reaction equation

HRID 1900744 reaction equation
Cl.[NH2:2][CH2:3][CH:4]1[O:18][C:7]2=[C:8]3[C:13](=[C:14]([CH3:16])[CH:15]=[C:6]2[CH:5]1[CH3:19])[NH:12][C:11](=[O:17])[CH:10]=[CH:9]3.[H][H]>O.[C].[Pd]>[NH2:2][CH2:3][CH:4]1[O:18][C:7]2=[C:8]3[C:13](=[C:14]([CH3:16])[CH:15]=[C:6]2[CH:5]1[CH3:19])[NH:12][C:11](=[O:17])[CH2:10][CH2:9]3

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 67771097HCID 67771097, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67770865HCID 67770865, compoundYield 82.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 962WaterSolvent

Procedure

The hydrochloric acid salt of (2RS,3SR)-2-aminomethyl-3,5-dimethyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-one obtained in Example 12 (575 mg, 2.05 mmol) in water (20 ml) was combined with 10% palladium-carbon (600 mg), then stirred in the presence of hydrogen gas at 80° C. for 4 hours. From the reaction mixture, palladium-carbon was filtered off. Water was distilled off under reduced pressure, and the residue was recrystallized from a solvent mixture of methanol--ether. As a result, 416 mg of a hydrochloric acid salt of (2 RS, 3 SR)-2-aminomethyl-3,5-dimethyl-2,3,6,7,8,9-hexahydrofuro-[2,3-f]quinoline-7-one was obtained as colorless crystals (71.8%). mp. >300° C.

Workup

  1. filtrationFrom the reaction mixture, palladium-carbon was filtered off
  2. distillationWater was distilled off under reduced pressure
  3. customthe residue was recrystallized from a solvent mixture of methanol

Sources & evidence

ORD record
ord-20df2a00f2f84d1986a12395c4c77354
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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