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

HRID 557572Notes

Reaction equation

HRID 557572 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-3743a373b28e4054ad10f493fb8a9e1c
Source dataset
uspto-grants-2011_11
Patent number
US08058441B2

Reaction notes

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