Lithium Hydroxide → 2-((2,2,2-Trifluoroethyl)amino)quinoline-7-carboxylic acid

HRID 711109Notes

Reaction equation

HRID 711109 reaction equation
[F:1][C:2]([F:20])([F:19])[CH2:3][NH:4][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][C:9]([C:15]([O:17]C)=[O:16])=[CH:10][CH:11]=2)[N:6]=1.[OH-].[Li+]>O1CCCC1>[F:20][C:2]([F:1])([F:19])[CH2:3][NH:4][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][C:9]([C:15]([OH:17])=[O:16])=[CH:10][CH:11]=2)[N:6]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67491717Methyl 2-((2,2,2-trifluoroethyl)amino)quinoline-7-carboxylate

Product 1

HCID 674915972-((2,2,2-Trifluoroethyl)amino)quinoline-7-carboxylic acidYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-((2,2,2-trifluoroethyl)amino)quinoline-7-carboxylate (172 mg, 0.605 mmol) in tetrahydrofuran (5 mL) was added aqueous lithium hydroxide (1.82 mL, 1.82 mmol, 1M solution) at room temperature. The reaction was stirred for 2.5 days. The solvent was removed under reduced pressure and the residue was acidified with 1N aqueous hydrochloric acid. The resulting precipitate was filtered and dried to give the title compound (65 mg, 40%) +ESI (M+H) 271.1, 1H NMR (400 MHz, DMSO-d6, δ): 4.31-4.41 (m, 2H) 7.01 (d, J=8.87 Hz, 1H) 7.69-7.80 (m, 2H) 8.06 (d, J=8.66 Hz, 1H) 8.14 (s, 1H) 13.03 (bs, 1H)

Workup

  1. customThe solvent was removed under reduced pressure
  2. filtrationThe resulting precipitate was filtered
  3. customdried

Sources & evidence

ORD record
ord-a5facf45a9884a2d970bf9ef1be9e7b3
Source dataset
uspto-grants-2015_11
Patent number
US09181252B2

Reaction notes

Loading…