Sodium Hydroxide → HCID 66637046, compound

HRID 1094668Notes

Reaction equation

HRID 1094668 reaction equation
[C:1]([C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[C:10]([C:15]([O:17]CC)=[O:16])[CH:11]=[N:12]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C(O)C>[C:1]([C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[C:10]([C:15]([OH:17])=[O:16])[CH:11]=[N:12]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66637141HCID 66637141, compound

Product 1

HCID 66637046HCID 66637046, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of Ethyl 7-tert-butylquinoline-3-carboxylate (1.63 g, 6.33 mmol) in 2M sodium hydroxide aqueous solution (6.4 ml, 12.8 mmol) and ethanol (50 ml) was heated at 75° C. for 2 hours. After the solvent was evaporated in vacuo, the residue was diluted with water. The aqueous solution was acidified to pH3 with 2M hydrochloric acid aqueous solution with ice-cooling and extracted with ethyl acetate. The combined solution was washed with brine, dried over sodium sulfate and concentrated in vacuo to give crude product, which was recrystallized from ethyl acetate and hexane to give the title compound (1.27 g, 88%) as a white solid. MS (ESI) m/z 228 (M−H)−, 230 (M+H)+. LC-MS: 2.46 min (Neutral full range 4—96)

Workup

  1. customAfter the solvent was evaporated in vacuo
  2. additionthe residue was diluted with water
  3. temperaturecooling
  4. extractionextracted with ethyl acetate
  5. washThe combined solution was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customto give crude product, which
  9. customwas recrystallized from ethyl acetate and hexane

Sources & evidence

ORD record
ord-3d6d7784461f4583a83ea947d20bbbeb
Source dataset
uspto-grants-2012_03
Patent number
US08134004B2

Reaction notes

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