Hydrochloric Acid → Methyl 3-(aminomethyl)-2-isobutyl-4-(4-methylphenyl)quinoline-6-carboxylate dihydrochloride

HRID 1986455Notes

Reaction equation

HRID 1986455 reaction equation
C(OC([NH:8][CH2:9][C:10]1[C:11]([CH2:31][CH:32]([CH3:34])[CH3:33])=[N:12][C:13]2[C:18]([C:19]=1[C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=1)=[CH:17][C:16]([C:27]([O:29][CH3:30])=[O:28])=[CH:15][CH:14]=2)=O)(C)(C)C.[ClH:35]>O1CCOCC1>[ClH:35].[ClH:35].[NH2:8][CH2:9][C:10]1[C:11]([CH2:31][CH:32]([CH3:34])[CH3:33])=[N:12][C:13]2[C:18]([C:19]=1[C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=1)=[CH:17][C:16]([C:27]([O:29][CH3:30])=[O:28])=[CH:15][CH:14]=2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68831784Methyl 3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-4-(4-methylphenyl)quinoline-6-carboxylate

Product 1

HCID 68828753Methyl 3-(aminomethyl)-2-isobutyl-4-(4-methylphenyl)quinoline-6-carboxylate dihydrochlorideYield 92%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To methyl 3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-4-(4-methylphenyl)quinoline-6-carboxylate (0.10 g, 0.22 mmol) was added 4N solution of hydrogen chloride in 1,4-dioxane (5 ml), and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated under reduced pressure, and the residue was crystallized from ethyl acetate to give methyl 3-(aminomethyl)-2-isobutyl-4-(4-methylphenyl)quinoline-6-carboxylate dihydrochloride (0.12 g, yield 92%) as white crystals.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-c0860ab333de48da8b4b7c68f46feff9
Source dataset
uspto-grants-2009_06
Patent number
US07547710B2

Reaction notes

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