Hydrochloric Acid → 5-[2-(2,5-Dimethoxyphenyl)ethyl]-2-amino benzoic acid methylester

HRID 1603538Notes

Reaction equation

HRID 1603538 reaction equation
[CH3:1][O:2][C:3](=[O:26])[C:4]1[CH:9]=[C:8]([CH2:10][CH2:11][C:12]2[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:13]=2[O:20][CH3:21])[CH:7]=[CH:6][C:5]=1[NH:22]C(=O)C.Cl.[OH-].[Na+]>CO>[CH3:1][O:2][C:3](=[O:26])[C:4]1[CH:9]=[C:8]([CH2:10][CH2:11][C:12]2[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:13]=2[O:20][CH3:21])[CH:7]=[CH:6][C:5]=1[NH2:22]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 54506424HCID 54506424, compound

Product 1

HCID 544614515-[2-(2,5-Dimethoxyphenyl)ethyl]-2-amino benzoic acid methylester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

87 mg of 5-[2-(2,5-dimethoxyphenyl)ethyl]-2-acetylamino benzoic acid methylester are dissolved in 6 ml of methanol, treated with 1 ml of 4 N hydrochloric acid and stirred for 48 hours at room temperature. The mixture is neutralised by addition of 2 N aqueous sodium hydroxide solution and extracted with ethyl acetate. The combined organic layers are dried over magnesium sulfate and concentrated in vacuo. Purification by chromatography on silica gel (hexane/ethyl acetate=6/1) yields the title compound as colourless crystals. mp: 50-55°.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic layers are dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customPurification by chromatography on silica gel (hexane/ethyl acetate=6/1)

Sources & evidence

ORD record
ord-0ee45fcd50ae477ea0bd43f15ef67435
Source dataset
uspto-grants-1999_11
Patent number
US05990116

Reaction notes

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