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

HRID 5374Notes

Reaction equation

HRID 5374 reaction equation
[NH2:1][C:2]1[C:11]([Cl:12])=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[C:4]([O:13][CH2:14][C:15]([N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])=[O:16])[CH:3]=1.CO.[OH-].[Na+].Cl>O>[NH2:1][C:2]1[C:11]([Cl:12])=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[C:4]([O:13][CH2:14][C:15]([N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])=[O:16])[CH:3]=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 68.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 4-amino-5-chloro-2-[2-(diethylamino)-2-oxoethoxy]benzoic acid, methyl ester (7.87 g, 25 mmol) 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 until a precipitate formed (pH 3), and the solid was collected, washed with water, air dried, and recrystallized from 2-propanol to afford (2 crops) 5.12 g (68%) of fine colorless needles; mp 186.5°-188.0° C.

Workup

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

Sources & evidence

ORD record
ord-d21c947da703415f83c8dca17871db03
Source dataset
uspto-grants-1993_09
Patent number
US05244907

Reaction notes

Loading…