HCID 70446579, compound → HCID 54150638, compound

HRID 464024Notes

Reaction equation

HRID 464024 reaction equation
Cl.[CH2:2]([N:4]([CH2:18][CH3:19])[CH2:5][CH:6]=[CH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=1)[CH3:3]>C(O)(=O)C.O.[Fe]>[CH2:18]([N:4]([CH2:2][CH3:3])[CH2:5][CH:6]=[CH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=1)[CH3:19]

Participants

5

Reactant 1

HCID 70446579HCID 70446579, compound

Product 1

HCID 54150638HCID 54150638, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a solution of 25 g (0.45 mole) of iron filings in 200 ml acetic acid, add a solution of 8.5 g (0.03 mole) N,N-diethyl-4-(4-nitrophenyl)-2-buten-1-amine hydrochloride in 50 ml water. Temperature rises to about 40° C., stir for 2 hr then filter off the excess iron. Adjust the pH of the filtrate to about 12 with sodium hydroxide, and extract with 3×100 ml methylene chloride. Take the combined extracts, dry over Na2SO4, then treat with charcoal. Evaporate the solvent to provide the title compound.

Workup

  1. customrises to about 40° C.
  2. filtrationthen filter off the excess iron
  3. extractionextract with 3×100 ml methylene chloride
  4. dry with materialdry over Na2SO4
  5. additiontreat with charcoal
  6. customEvaporate the solvent

Sources & evidence

ORD record
ord-c264c34153014a8d9f4026922cbaba42
Source dataset
uspto-grants-1985_10
Patent number
US04545995

Reaction notes

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