Sodium Hydroxide → 2-(Trifluoromethyl)-5,6,7,8-tetrahydroquinoline-6-carboxylic acid

HRID 1690789Notes

Reaction equation

HRID 1690789 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:12]=[CH:11][C:10]2[CH2:9][CH:8]([C:13]([O:15]C)=[O:14])[CH2:7][CH2:6][C:5]=2[N:4]=1.[OH-].[Na+]>CO>[F:18][C:2]([F:1])([F:17])[C:3]1[CH:12]=[CH:11][C:10]2[CH2:9][CH:8]([C:13]([OH:15])=[O:14])[CH2:7][CH2:6][C:5]=2[N:4]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58118640Methyl 2-(trifluoromethyl)-5,6,7,8-tetrahydroquinoline-6-carboxylate

Product 1

HCID 581186312-(Trifluoromethyl)-5,6,7,8-tetrahydroquinoline-6-carboxylic acidYield 122.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
90 °C

Procedure

A 25 mL flask was charged with methyl 2-(trifluoromethyl)-5,6,7,8-tetrahydroquinoline-6-carboxylate (6 mg, 0.02 mmol), methanol (3 mL) and 1 M aqueous sodium hydroxide (0.23 mL, 10 equiv), and the mixture heated in an oil bath at 90° C. The mixture was removed from the heat after 1.5 h, diluted with 1M NaH2PO4 (10 mL), buffered to pH 3 with 1M H3PO4, then extracted with DCM (3×20 mL). The combined organic extracts were dried (Na2SO4), filtered, and concentrated to afford the acid as a white solid (6 mg, 100%). 1H NMR (400 MHz, CDCl3) δ 7.59 (d, J=8.0 Hz, 1H), 7.46 (d, J=8.0 Hz, 1H), 3.21-3.02 (m, 4H), 2.95-2.84 (m, 1H), 2.42-2.32 (m, 1H), 2.14-2.03 (m, 1H), 1.10 (br s, 11-1); m/z=246.4 (M+H)f.

Workup

  1. customThe mixture was removed from the
  2. temperatureheat after 1.5 h
  3. additiondiluted with 1M NaH2PO4 (10 mL)
  4. extractionextracted with DCM (3×20 mL)
  5. dry with materialThe combined organic extracts were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f94d8f465092422eab8c8c2b43cee6e8
Source dataset
uspto-grants-2012_04
Patent number
US08153651B2

Reaction notes

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