Water → 1-Acetyl-4-phenyl-1,2,3,4-tetrahydro-2,2,4-trimethylquinoline-6-carboxylic acid

HRID 2382291Notes

Reaction equation

HRID 2382291 reaction equation
[OH-].[Na+].C[O:4][C:5]([C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]([C:17](=[O:19])[CH3:18])[C:12]([CH3:21])([CH3:20])[CH2:11][C:10]2([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH3:22])=[O:6].O>O1CCOCC1.O>[C:17]([N:13]1[C:14]2[C:9](=[CH:8][C:7]([C:5]([OH:6])=[O:4])=[CH:16][CH:15]=2)[C:10]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([CH3:22])[CH2:11][C:12]1([CH3:21])[CH3:20])(=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 669924761-Acetyl-4-phenyl-1,2,3,4-tetrahydro-2,2,4-trimethylquinoline-6-carboxylic acid methyl ester

Product 1

HCID 179628841-Acetyl-4-phenyl-1,2,3,4-tetrahydro-2,2,4-trimethylquinoline-6-carboxylic acid

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

A 2 M NaOH solution was added dropwise to a stirred solution of 1-acetyl-4-phenyl-1,2,3,4-tetrahydro-2,2,4-trimethylquinoline-6-carboxylic acid methyl ester (1.2 g) in dioxane/water 4:1 (v/v) (50 ml) until pH 12. After stirring for 18 h, the reaction mixture was poured into water and extracted with ethyl acetate at pH 2. The organic layer was washed with water and brine, dried (MgSO4) and concentrated in vacuo.

Workup

  1. extractionextracted with ethyl acetate at pH 2
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7d7d59b9b2c34bb99a227938688daa65
Source dataset
uspto-grants-2012_09
Patent number
US08258293B2

Reaction notes

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