Trifluoroacetic acid → 2-(1-Methyl-2-oxo-1,2-dihydroquinoline-3-carboxamido)acetic acid

HRID 905918Notes

Reaction equation

HRID 905918 reaction equation
FC(F)(F)C(O)=O.[CH3:8][N:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[C:11]([C:19]([NH:21][CH2:22][C:23]([O:25]C(C)(C)C)=[O:24])=[O:20])[C:10]1=[O:30]>>[CH3:8][N:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[C:11]([C:19]([NH:21][CH2:22][C:23]([OH:25])=[O:24])=[O:20])[C:10]1=[O:30]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67388284Tert-butyl 2-(1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamido)acetate

Product 1

HCID 593400592-(1-Methyl-2-oxo-1,2-dihydroquinoline-3-carboxamido)acetic acidYield 29%

Procedure

Trifluoroacetic acid (1.00 ml, 13 mmol) was added to tert-butyl 2-(1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamido)acetate (0.021 g, 0.07 mmol) and stirred at room temperature for 15 minutes. Trifluoroacetic acid was removed under vacuum and the resulting solids were washed with water (3×), ether (3×) and dried in a vacuum oven at 50° C. to afford 2-(1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamido)acetic acid in 29% yield.

Workup

  1. customTrifluoroacetic acid was removed under vacuum
  2. washthe resulting solids were washed with water (3×), ether (3×)
  3. customdried in a vacuum oven at 50° C.

Sources & evidence

ORD record
ord-193cdb017cf64429a44eb9b477ac4618
Source dataset
uspto-grants-2011_09
Patent number
US08012968B2

Reaction notes

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