Water → 4-Amino-5-chloro-2-(2-methoxyethoxy)benzoic acid methyl ester

HRID 2254609Notes

Reaction equation

HRID 2254609 reaction equation
[H-].[Na+].[NH2:3][C:4]1[C:13]([Cl:14])=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([OH:15])[CH:5]=1.[CH3:16][O:17][CH2:18][CH2:19]Br.O>CN(C)C=O>[NH2:3][C:4]1[C:13]([Cl:14])=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([O:15][CH2:19][CH2:18][O:17][CH3:16])[CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 14883223Methyl 4-amino-5-chloro-2-hydroxybenzoate

Product 1

HCID 539320764-Amino-5-chloro-2-(2-methoxyethoxy)benzoic acid methyl esterYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 60% sodium hydride/oil dispersion (1.0 g, 25 mmoles) in anhydrous dimethylformamide (40 ml) under nitrogen was treated with methyl 4-amino-5-chloro-2-hydroxybenzoate (4.03 g, 20 mmoles), stirred for 30 minutes, then treated with 2-bromoethyl methyl ether (3.48 g, 25 mmoles). The mixture was heated to 95°±5° C. for 1.5 hours, then cooled and added to water (250 ml). The aqueous suspension was filtered, and the solid was washed with water, air dried, and recrystallized from ether/hexane to yield 2.75 g (53%) of product, 121°-122.5° C.

Workup

  1. temperatureThe mixture was heated to 95°±5° C. for 1.5 hours
  2. temperaturecooled
  3. filtrationThe aqueous suspension was filtered
  4. washthe solid was washed with water, air
  5. customdried
  6. customrecrystallized from ether/hexane

Sources & evidence

ORD record
ord-210c0c3b4ec84d3a87beaa028b474a96
Source dataset
uspto-grants-1993_08
Patent number
US05236931

Reaction notes

Loading…