Hydrochloric Acid → HCID 86746849, compound

HRID 248877Notes

Reaction equation

HRID 248877 reaction equation
C[O:2][C:3](=O)[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.[NH2:27][NH2:28]>[Cl-].[Na+].O>[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]([NH:27][NH2:28])=[O:2])[CH:16]=[CH:15][CH:14]=1)[CH3:18])(=[O:23])[CH3:22]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9321HydrazineHCID 54429507HCID 54429507, compound

Product 1

HCID 86746849HCID 86746849, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

2[[3-[1-(Acetylhydroxyamino)ethyl]-2-chlorophenyl]amino]benzoic acid methyl ester (4.0 g, 11.0 mmoles) is suspended in neat hydrazine (30 mL) and stirred at room temperature. When all solid is dissolved (approximately 10 minutes after addition) the reaction mixture is diluted with 300 mL of cold brine. The pH of the solution is lowered to pH 7 by the addition of concentrated HCl. The precipitate is collected by filtration and recrystallized from EtOAc to give 2-[[3-[1-(acetylhydroxyamino]ethyl]-2-chlorophenyl]amino]benzoic acid hydrazide (2.8 g, 69%); m.p. 193°-195° C.

Workup

  1. dissolutionWhen all solid is dissolved
  2. addition(approximately 10 minutes after addition) the reaction mixture
  3. filtrationThe precipitate is collected by filtration
  4. customrecrystallized from EtOAc

Sources & evidence

ORD record
ord-0ef38f85e5834016897c73451570cb5c
Source dataset
uspto-grants-1993_05
Patent number
US05212189

Reaction notes

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