Ethyl Acetate → HCID 67441465, compound

HRID 2045536Notes

Reaction equation

HRID 2045536 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:17]([CH3:19])([CH3:18])[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:20]([O:22]C)=[O:21])[CH:14]=3)[NH:9]2)[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+].C(OCC)(=O)C>CO.O>[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:17]([CH3:18])([CH3:19])[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:20]([OH:22])=[O:21])[CH:14]=3)[NH:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 67442023HCID 67442023, compound

Product 1

HCID 67441465HCID 67441465, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

Methyl 2-(3-aminophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (100 mg, 0.32 mmol) and sodium hydroxide (0.2 g, 5 mmol) was dissolved in methanol/water (10 mL/2 mL) and the reaction mixture was allowed to reflux for 1.5 h. Thin layer chromatography (petroleum ether:ethyl acetate=3:1, Rf=0.1) showed the reaction was complete. The solvent was removed in vacuo and the residue was acidified with 1 M hydrochloric acid solution to pH=6. The precipitated off-white solid was collected by filtration and dissolved in 50 ml of acetone, dried over sodium sulfate. Filtered and concentrated, the residue was recrystallization from dichloromethane/hexane to afford 78 mg of 2-(3-aminophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid, Yield: 82.1%, MS (ES+APCI) M+1=297.1.

Workup

  1. temperatureto reflux for 1.5 h
  2. customThe solvent was removed in vacuo
  3. filtrationThe precipitated off-white solid was collected by filtration
  4. dissolutiondissolved in 50 ml of acetone
  5. dry with materialdried over sodium sulfate
  6. filtrationFiltered
  7. concentrationconcentrated
  8. customrecrystallization from dichloromethane/hexane

Sources & evidence

ORD record
ord-8c5787000aff41d5aa76f104cb52c37f
Source dataset
uspto-grants-2013_11
Patent number
US08586747B2

Reaction notes

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