Hydrochloric Acid → 4-Dimethylaminomethyl-3-methoxy-benzoic acid

HRID 1958810Notes

Reaction equation

HRID 1958810 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11]C)=[O:10])=[CH:7][C:6]=1[O:15][CH3:16])[CH3:3].Cl>CO.[OH-].[Na+]>[CH3:3][N:2]([CH2:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([OH:11])=[O:10])=[CH:7][C:6]=1[O:15][CH3:16])[CH3:1]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 21182956Methyl 4-(Dimethylamino)methyl-3-methoxybenzoate

Product 1

HCID 211828904-Dimethylaminomethyl-3-methoxy-benzoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl 4-dimethylaminomethyl-3-methoxy-benzoate (420 mg, 1.88 mmol) in MeOH (4 mL), 1 M aq. NaOH solution (2.5 mL) was added. The mixture was stirred at 50° C. for 2 h and at rt for 16 h before it was neutralised by adding 1 M aq. HCl (1.25 mL) and the solvent was evaporated. The residue was suspended in n-butanol (100 mL) and the mixture was refluxed for 1 h. The suspension was cooled to rt, filtered and the filtrate was concentrated and dried to give 4-dimethylaminomethyl-3-methoxy-benzoic acid as a colourless resin (380 mg). LC-MS*: tR=0.44 min, [M+1]+=210.32.

Workup

  1. customthe solvent was evaporated
  2. temperaturethe mixture was refluxed for 1 h
  3. temperatureThe suspension was cooled to rt
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customdried

Sources & evidence

ORD record
ord-ea34d2e786d54129ae5a47dccda74079
Source dataset
uspto-grants-2013_04
Patent number
US08410151B2

Reaction notes

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