Hydrochloric Acid → HCID 19762618, compound

HRID 2051243Notes

Reaction equation

HRID 2051243 reaction equation
C[O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH:17]([N:19]([C:21](=[O:23])[CH3:22])[OH:20])[CH3:18])[C:12]=1[Cl:24].Cl>[OH-].[K+]>[C:21]([N:19]([OH:20])[CH:17]([C:13]1[C:12]([Cl:24])=[C:11]([NH:10][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([OH:25])=[O:2])[CH:16]=[CH:15][CH:14]=1)[CH3:18])(=[O:23])[CH3:22]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54429507HCID 54429507, compound

Product 1

HCID 19762618HCID 19762618, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

2-[[3-[1-(Acetylhydroxyamino)ethyl]-2-chlorophenyl]amino]benzoic acid methyl ester (0.24 g, 0.7 mmol) is suspended in 150 mL of 1 N potassium hydroxide containing 10 mL methanol. The reaction mixture is stirred until all the solid is dissolved (about 2 hours). It is acidified to pH=1 with concentrated HCl and the resulting precipitate is collected by filtration. Recrystallization from ethyl acetate gives 2-[[3-[1-[acetylhydroxyamino)ethyl]-2-chlorophenyl]amino]benzoic acid (74 mg, 32 %) as a hydrate. mp=162-164° C. dec.

Workup

  1. dissolutionis dissolved (about 2 hours)
  2. filtrationthe resulting precipitate is collected by filtration
  3. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-4674080a30a3443987d83617e6ee297a
Source dataset
uspto-grants-1991_05
Patent number
US05017604

Reaction notes

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