Hydrochloric Acid → 5-Chloro-2-[2-(phenylmethyl)hydrazinyl]benzoic acid

HRID 1681693Notes

Reaction equation

HRID 1681693 reaction equation
C([BH3-])#N.[Na+].[CH:5](=[N:12][NH:13][C:14]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:15]=1[C:16]([OH:18])=[O:17])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl>CO.C1COCC1.O>[CH2:5]([NH:12][NH:13][C:14]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:15]=1[C:16]([OH:18])=[O:17])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 5003444Sodium cyanoborohydrideHCID 67898655HCID 67898655, compound

Product 1

HCID 198054755-Chloro-2-[2-(phenylmethyl)hydrazinyl]benzoic acidYield 91.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of sodium cyanoborohydride (780 mg) in methanol (20 ml) was added to a stirred solution of 2-(benzylidenehydrazino)-5-chlorobenzoic acid (2.7 g) in THF (20 ml) containing a few milligrams of the indicator Congo Red. A methanolic solution of hydrogen chloride was added dropwise until the indicator in the reaction solution turned blue. Stirring was continued for 15 minutes. The reaction mixture was diluted with water and extracted with ethyl acetate. The extracts were washed with brine, dried (MgSO4) and evaporated to give 2-(2-benzylhydrazino)-5-chlorobenzoic acid as a solid (2.5 g) which was used without purification.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-6189a1360f0c45beb66adc9576c280a2
Source dataset
uspto-grants-1992_12
Patent number
US05173496

Reaction notes

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