Phosphoric Acid → 2-(1,1,1-Trifluoro-2-methylpropan-2-yl)-5,6,7,8-tetrahydroquinoline-6-carboxylic acid

HRID 1697452Notes

Reaction equation

HRID 1697452 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]([C:6]1[CH:15]=[CH:14][C:13]2[CH2:12][CH:11]([C:16]([O:18]C)=[O:17])[CH2:10][CH2:9][C:8]=2[N:7]=1)([CH3:5])[CH3:4].[OH-].[Na+].OP(O)(O)=O>CO.O>[F:21][C:2]([F:1])([F:20])[C:3]([C:6]1[CH:15]=[CH:14][C:13]2[CH2:12][CH:11]([C:16]([OH:18])=[O:17])[CH2:10][CH2:9][C:8]=2[N:7]=1)([CH3:5])[CH3:4]

Participants

6

Reactant 3

HCID 1004Phosphoric AcidHCID 14798Sodium HydroxideHCID 58118628Methyl 2-(1,1,1-trifluoro-2-methylpropan-2-yl)-5,6,7,8-tetrahydroquinoline-6-carboxylate

Product 1

HCID 581186242-(1,1,1-Trifluoro-2-methylpropan-2-yl)-5,6,7,8-tetrahydroquinoline-6-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of methyl 2-(1,1,1-trifluoro-2-methylpropan-2-yl)-5,6,7,8-tetrahydroquinoline-6-carboxylate (0.97 g, 3.2 mmol) in methanol (20 mL) was treated with 1 M aqueous sodium hydroxide (6 mL, 2 equiv), and the mixture was heated to reflux. After 1.5 h the cooled mixture was diluted with water (40 mL), adjusted to pH 6 with H3PO4, and extracted with DCM (3×20 mL). The combined organic layers were dried (Na2SO4), filtered and concentrated to a solid (0.76 g, 82%). 1H NMR (400 MHz, DMSO-d6) δ 12.34 (br s, 1H), 7.55 (d, J=8.1 Hz, 1H), 7.41 (d, J=8.1 Hz, 1H), 2.99-2.83 (m, 4H), 2.77-2.69 (m, 1H), 2.19-2.11 (m, 1H), 1.91-1.81 (m, 1H), 1.54 (s, 6H); m/z=288.4 (M+H)+.

Workup

  1. temperaturethe mixture was heated to reflux
  2. extractionextracted with DCM (3×20 mL)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated to a solid (0.76 g, 82%)

Sources & evidence

ORD record
ord-9a92b85c362f4ac4a5cc2714c4c04f9e
Source dataset
uspto-grants-2012_04
Patent number
US08163901B2

Reaction notes

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