Lithium Hydroxide → (2-Chloro-6-dimethylaminomethyl-naphthalen-1-yl)-acetic acid

HRID 639197Notes

Reaction equation

HRID 639197 reaction equation
C([O:3][C:4](=[O:21])[CH2:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([CH2:16][N:17]([CH3:19])[CH3:18])=[CH:13][CH:14]=2)[CH:9]=[CH:8][C:7]=1[Cl:20])C.[OH-].[Li+].OS([O-])(=O)=O.[Na+]>O1CCOCC1.O>[Cl:20][C:7]1[CH:8]=[CH:9][C:10]2[C:15](=[CH:14][CH:13]=[C:12]([CH2:16][N:17]([CH3:18])[CH3:19])[CH:11]=2)[C:6]=1[CH2:5][C:4]([OH:21])=[O:3]

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 516919Sodium BisulfateHCID 68704219(2-Chloro-6-dimethylaminomethyl-naphthalen-1-yl)-acetic acid ethyl ester

Product 1

HCID 68706916(2-Chloro-6-dimethylaminomethyl-naphthalen-1-yl)-acetic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

(2-Chloro-6-dimethylaminomethyl-naphthalen-1-yl)-acetic acid ethyl ester (223 mg, 0.73 mmol) is dissolved in dioxane (2.6 ml). Water (0.96 ml) and lithium hydroxide (21 mg, 0.88 mmol) are then added, and the reaction mixture is warmed to 60° C. for 4 h. HPLC analysis indicates complete conversion of starting material. The reaction is diluted with water, adjusted to pH 6-7 by addition of 1 M aqueous NaHSO4, and extracted with EtOAc. The water layer is then concentrated, and the solid residue is repeatedly extracted with MeOH to yield pure title compound. ES+-MS: 278.3, 280.1 [M+H]+.

Workup

  1. extractionextracted with EtOAc
  2. concentrationThe water layer is then concentrated
  3. extractionthe solid residue is repeatedly extracted with MeOH

Sources & evidence

ORD record
ord-17c96eb9efed46f8a778ade623572b59
Source dataset
uspto-grants-2010_04
Patent number
US07691861B2

Reaction notes

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