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

HRID 846600

Reaction equation

HRID 846600 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>[CH3:11][O:10][C:8](=[O:9])[C:7]1[CH:12]=[C:13]([Cl:14])[C:4]([NH2:3])=[CH:5][C:6]=1[O:15][CH2:19][CH2:18][O:17][CH3:16]

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 (1.00 g, 0.025 mole) in anhydrous dimethylformamide (40 ml) under nitrogen was treated with 4-amino-5-chloro-2-hydroxybenzoic acid, methyl ester (4.03 g, 0.020 mole), stirred for 30 minutes, then treated with 2-bromoethyl methyl ether (3.48 g, 0.025 mole). 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, collected, and recrystallized from ether/hexane to afford 2.75 g (53%) of 4-amino-5-chloro-2-(2-methoxyethoxy)benzoic acid methyl ester; mp 121.0°-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. customcollected
  7. customrecrystallized from ether/hexane

Sources & evidence

ORD record
ord-3f35d3bd5374491abc572606c4ab654a
Source dataset
uspto-grants-1992_08
Patent number
US05137895

Linked notes

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