2-Chlorophenylhydrazine hydrochloride → HCID 86594817, compound

HRID 915839Notes

Reaction equation

HRID 915839 reaction equation
[Li].[CH2:2]([O:4][C:5](=[O:18])[C:6](O)=[CH:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)=[O:9])[CH3:3].[N:19]([O-:21])=O.[Na+].Cl.[Cl:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[NH:31][NH2:32]>C(O)(=O)C>[CH2:2]([O:4][C:5](=[O:18])[C:6](=[N:32][NH:31][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[Cl:24])[CH:7]([N:19]=[O:21])[C:8]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)=[O:9])[CH3:3]

Participants

5

Reactant 3

HCID 4432872-Chlorophenylhydrazine hydrochlorideHCID 23668193Sodium NitriteHCID 178473082HCID 178473082, compound

Product 1

HCID 86594817HCID 86594817, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
10 °C

Procedure

4-(4-Chlorophenyl)-2-hydroxy-4-oxobut-2-enoic acid ethyl ester lithium salt (10 g, 38.37 mmol) was dissolved in acetic acid (400 ml). After the solution was cooled to 10° C. with an ice-water bath, a concentrated aqueous solution of sodium nitrite (2.86 g, 40.29 mmol) was added dropwise, keeping the temperature between 10 and 15° C. The reaction mixture was stirred for another 45 minutes, and 2-chlorophenylhydrazine HCl salt (8.5 g, 46.04 mmol) was added in portions. Stirring was continued for 3 hours. Upon completion of the reaction, the reaction mixture was poured into 600 ml ice-cold water. A yellow solid precipitated and after 2 hours, it was collected, washed with water, and dried to give crude 4-(4-chlorophenyl)-2-[(2-chlorophenyl)hydrazono]-3-nitroso-4-oxobutyric acid ethyl ester which was used in the next step without further purification.

Workup

  1. customthe temperature between 10 and 15° C
  2. stirringStirring
  3. waitwas continued for 3 hours
  4. customUpon completion of the reaction
  5. customA yellow solid precipitated and after 2 hours
  6. customit was collected
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-8e569da1ee3d4f28ad4f362f5484fe2f
Source dataset
uspto-grants-2007_09
Patent number
US07268133B2

Reaction notes

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