Water → HCID 54588451, compound

HRID 2169840Notes

Reaction equation

HRID 2169840 reaction equation
COC1C=CC(C[NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3[CH3:19])[N:12]=[C:11]([CH3:20])[C:10]=2[C:21]([O:23]CC)=[O:22])=CC=1.[OH-].[Na+].O>C(O)(C(F)(F)F)=O.CCO>[NH2:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[CH3:19])[N:12]=[C:11]([CH3:20])[C:10]=1[C:21]([OH:23])=[O:22]

Participants

6

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 66745563HCID 66745563, compound

Product 1

HCID 54588451HCID 54588451, compoundYield 90.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
100 °C

Procedure

Ethyl 4-(4-methoxybenzylamino)-2,5-dimethylquinoline-3-carboxylate (Example 12a, 0.563 g, 1.54 mmol) was dissolved in TFA (8 mL) and the resultant solution was stirred at room temperature for 15 minutes, TFA was then removed under vacuum to give the crude ethyl 4 product, which was dissolved in EtOH (4 mL). To this solution was added NaOH (4.0 N, 3.86 mL) and the reaction mixture was stirred at 100° C. for 1 hr. Water (25 mL) was added, and the solvent was decanted away from insoluble material then acidified with AcOH to pH 5.5. The precipitate was collected by filtration to give the title compound (300 mg, 90%) as a white solid. 1H NR (400 MHz, DMSO-d6) δ 2.78 (s, 3H), 2.88 (s, 3H), 7.30 (d, J=7.2 Hz, 1H), 7.58 (d, J=8.0 Hz, 1H), 7.65 (m, 1H), 7.8-8.0 (br, 1H), 12.2-12.9 (br, 2H). MS 217 (MH+).

Workup

  1. customTFA was then removed under vacuum
  2. customto give the crude ethyl 4 product, which
  3. customthe solvent was decanted away from insoluble material
  4. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-471bfb800ba64a2d90a47d0a9c41f10d
Source dataset
uspto-grants-2015_06
Patent number
US09049878B2

Reaction notes

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