Hydrochloric Acid → Benzoic acid, 2-[(carboxymethyl)methylamino]-5-methoxy-

HRID 653151Notes

Reaction equation

HRID 653151 reaction equation
[K].Br[C:3]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:4]=1[C:5]([OH:7])=[O:6].[OH-].[K+].[CH3:16][NH:17][CH2:18][C:19]([OH:21])=[O:20].C(=O)([O-])[O-].[K+].[K+].Cl>CC(O)C.O.[Cu]>[C:19]([CH2:18][N:17]([CH3:16])[C:3]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:4]=1[C:5]([OH:7])=[O:6])([OH:21])=[O:20]

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 1088SarcosineHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 899062-Bromo-5-methoxybenzoic acidHCID 5462222Potassium2×

Product 1

HCID 2727748Benzoic acid, 2-[(carboxymethyl)methylamino]-5-methoxy-Yield 86%

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

A mixture of 244 g (0.91 mole) of the potassium salt of 2-bromo-5-methoxybenzoic acid (prepared by treating a solution of the parent carboxylic acid in 2-propanol with excess methanolic potassium hydroxide), 196 g (1.54 mole) of the potassium salt of N-methylglycine (prepared as above), 13 g (0.82 mole) of anhydrous potassium carbonate and 0.66 g (0.01 mole) of copper powder in 220 ml of water was stirred at reflux for five hours. The mixture was cooled, added to 4.0 kg of ice/water, and acidified with concentrated hydrochloric acid to precipitate the crude product. THe solid was filtered and washed with water to yield 186 g (86% yield) of the carboxylic acid product. A sample recrystallized from aqueous 2-methoxyethanol was analytically pure, mp 196° C.-dec.

Workup

  1. customprepared
  2. temperatureat reflux for five hours
  3. temperatureThe mixture was cooled
  4. customto precipitate the crude product
  5. filtrationTHe solid was filtered
  6. washwashed with water

Sources & evidence

ORD record
ord-de45e2f90c1c408a921e03700e60a9f3
Source dataset
uspto-grants-1987_06
Patent number
US04675332

Reaction notes

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