Trifluoroacetic acid → HCID 59631180, compound

HRID 1431773Notes

Reaction equation

HRID 1431773 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:19]CC3C=CC(OC)=CC=3)=[C:7]([CH3:18])[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)=[N:9]2)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH2:19])=[C:7]([CH3:18])[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59631067HCID 59631067, compound

Product 1

HCID 59631180HCID 59631180, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 7-fluoro-N-(4-methoxybenzyl)-3-methyl-2-(pyridin-2-yl)quinolin-4-amine (0.900 g, 2.410 mmol), trifluoroacetic acid (2.8 mL, 36.2 mmol), and DCM (4 mL) was stirred at 23° C. for 1 hour. Upon completion, the reaction was concd, and the resulting residue was partitioned between EtOAc and 1 N HCl. The aqueous layer was then basified, and the product extracted twice with EtOAc. The combined organics were dried over magnesium sulfate and concd, affording 7-fluoro-3-methyl-2-(pyridin-2-yl)quinolin-4-amine as a beige amorphous solid. Mass Spectrum (ESI) m/e=254.2 (M+1).

Workup

  1. customthe resulting residue was partitioned between EtOAc and 1 N HCl
  2. extractionthe product extracted twice with EtOAc
  3. dry with materialThe combined organics were dried over magnesium sulfate and concd

Sources & evidence

ORD record
ord-10ae03fa55f94c9cb27cbf806449fa05
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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