Sodium Hydroxide → HCID 66913233, compound

HRID 2104485Notes

Reaction equation

HRID 2104485 reaction equation
[C:1]1([C:7]2[C:16]3[C:11](=[C:12]([C:17]([F:20])([F:19])[F:18])[CH:13]=[CH:14][CH:15]=3)[N:10]=[CH:9][C:8]=2[C:21]([O:23]CC)=[O:22])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>C1COCC1.CO>[C:1]1([C:7]2[C:16]3[C:11](=[C:12]([C:17]([F:19])([F:20])[F:18])[CH:13]=[CH:14][CH:15]=3)[N:10]=[CH:9][C:8]=2[C:21]([OH:23])=[O:22])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66913232HCID 66913232, compound

Product 1

HCID 66913233HCID 66913233, compoundYield 42.5%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

Ethyl 4-phenyl-8-(trifluoromethyl)quinoline-3-carboxylate (35.96 g, 104.14 mmol) was taken into THF/MeOH (300 mL of 1:1 mixture) along with 2 M NaOH (200 mL) and heated at 70° C. for 20 minutes. The organics were removed and the remaining aqueous layer was cooled to 0° C. and acidified with concentrated HCl. The mixture was concentrated and the resulting material was passed through a silica gel column using CH2Cl2, then 20% MeOH in CH2Cl2. The fractions were combined and the volume was reduced and then diluted to twice the volume with hexane and placed in a freezer overnight. A solid precipitated which was filtered and dried to yield the carboxylic acid as a brown solid (14.03 g). MS (ESI) m/z 318 ([M+H]+); MS (ESI) m/z 316 ([M−H]−).

Workup

  1. customThe organics were removed
  2. temperaturethe remaining aqueous layer was cooled to 0° C.
  3. concentrationThe mixture was concentrated
  4. additiondiluted to twice the volume with hexane
  5. customA solid precipitated which
  6. filtrationwas filtered
  7. customdried

Sources & evidence

ORD record
ord-67c27bf0287140f18f469b3c8525be4d
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

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