Hydrochloric Acid → 4-Cyanophenylhydrazine Hydrochloride

HRID 655868Notes

Reaction equation

HRID 655868 reaction equation
C(OC([N:8]([C:10]1[CH:15]=[CH:14][C:13]([C:16]#[N:17])=[CH:12][CH:11]=1)[NH2:9])=O)(C)(C)C.O1CCOCC1.[ClH:24]>C(Cl)Cl>[ClH:24].[NH:8]([C:10]1[CH:15]=[CH:14][C:13]([C:16]#[N:17])=[CH:12][CH:11]=1)[NH2:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 11230036N-(4-Cyano-phenyl)-hydrazinecarboxylic Acid tert-butyl Ester2×

Product 1

HCID 162129624-Cyanophenylhydrazine Hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Title compound 52A, N-(4-cyano-phenyl)-hydrazinecarboxylic acid tert-butyl ester (0.23 g, 1.0 eq, 0.99 mmol) was suspended in a mixture of 4M HCl in Dioxane (4.2 ml, 17.0 eq, 16.8 mmol) and DCM (5 ml). The mixture was then stirred at room temperature for 18 hours The resultant precipitate was isolated by filtration and washed with DCM to yield the title compound as a cream solid. (0.14 g, 0.8 mmol, 85%). 1H NMR (DMSO) 400 MHz: Indicates product in >95% purity

Workup

  1. customwas isolated by filtration
  2. washwashed with DCM

Sources & evidence

ORD record
ord-c859f5cb14dc4d8f84fc86e38cdd5bb9
Source dataset
uspto-grants-2011_12
Patent number
US08071607B2

Reaction notes

Loading…