HCID 66745563, compound → HCID 66746516, compound

HRID 2047727Notes

Reaction equation

HRID 2047727 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][CH2:24][CH3:25])=[O:22])=CC=1>C(O)(C(F)(F)F)=O>[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]([O:23][CH2:24][CH3:25])=[O:22]

Participants

3

Reactant 1

HCID 66745563HCID 66745563, compound

Product 1

HCID 66746516HCID 66746516, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

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-amino-2,5-dimethylquinoline-3-carboxylate 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 NMR (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

Sources & evidence

ORD record
ord-d2b446b5a7db4ecfb4e12e41602db670
Source dataset
uspto-grants-2013_11
Patent number
US08592592B2

Reaction notes

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