Hydrochloric Acid → 4-Amino-5-chloro-2-[2-(diethylamino)-2-oxoethoxy]benzoic acid

HRID 846605Notes

Reaction equation

HRID 846605 reaction equation
C[O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([Cl:10])[C:7]([NH2:11])=[CH:6][C:5]=1[O:12][CH2:13][C:14]([N:16]([CH2:19][CH3:20])[CH2:17][CH3:18])=[O:15].CO.[OH-].[Na+].Cl>O>[NH2:11][C:7]1[C:8]([Cl:10])=[CH:9][C:4]([C:3]([OH:21])=[O:2])=[C:5]([O:12][CH2:13][C:14]([N:16]([CH2:19][CH3:20])[CH2:17][CH3:18])=[O:15])[CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 537123184-Amino-5-chloro-2-[2-(diethylamino)-2-oxoethoxy]benzoic acid methyl ester

Product 1

HCID 197959844-Amino-5-chloro-2-[2-(diethylamino)-2-oxoethoxy]benzoic acidYield 68%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A solution of the ester (7.87 g, 25 mole) in water (70 g) containing methanol (40 g) was treated with 50% sodium hydroxide (10 g) and heated to 60° C. for 30 minutes. The mixture was neutralized with 3N HCl solution until a precipitate formed (pH~3). The solid was filtered, washed with water, air dried, and recrystallized from 2-propanol to afford (2 crops) 5.12 g (68%) of the title compound as fine colorless needles; mp 186.5°-188.0° C.

Workup

  1. customformed (pH~3)
  2. filtrationThe solid was filtered
  3. washwashed with water, air
  4. customdried
  5. customrecrystallized from 2-propanol

Sources & evidence

ORD record
ord-6b251af2bfa9403f872d46091b887372
Source dataset
uspto-grants-1992_08
Patent number
US05137895

Reaction notes

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