Hydrochloric Acid → HCID 23370066, compound

HRID 1901045Notes

Reaction equation

HRID 1901045 reaction equation
[CH3:1][N:2]([CH3:31])[C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH2:21]/[CH:22]=[C:23](/[CH2:25][CH2:26][CH:27]=[C:28]([CH3:30])[CH3:29])\[CH3:24])[C:10](=[O:20])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N+:17]([O-])=O)=[CH:5][CH:4]=1.Cl>C(O)C.[Fe]>[CH3:1][N:2]([CH3:31])[C:3]1[CH:4]=[CH:5][C:6]([N:9]([CH2:21]/[CH:22]=[C:23](/[CH2:25][CH2:26][CH:27]=[C:28]([CH3:30])[CH3:29])\[CH3:24])[C:10](=[O:20])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[NH2:17])=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 23370078HCID 23370078, compound

Product 1

HCID 23370066HCID 23370066, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

N-(4-dimethylaminophenyl)-N-geranyl-2-nitrobenzamide (2.5 g) was dissolved in ethanol (35 ml), to the solution was added 1N-aqueous HCl (6.5 ml) and iron powder (1.3 g), and the mixture was stirred under heat for 2 hrs. After filtering the insolubles, distilling off the solvent, and neutralizing with 10% sodium hydroxide solution, the mixture was extracted with ethyl acetate, washed with water and saturated saline and dried over anhydrous MgSO4. The solvent was distilled off. The residue was purified by a silica gel column chromatography (hexane:ethyl acetate=3:1) to give N-(4-dimethylaminophenyl)-N-geranyl-2-aminobenzamide 1.3 g (58%) as an oily product.

Workup

  1. temperatureunder heat for 2 hrs
  2. filtrationAfter filtering the insolubles
  3. distillationdistilling off the solvent
  4. extractionneutralizing with 10% sodium hydroxide solution, the mixture was extracted with ethyl acetate
  5. washwashed with water and saturated saline
  6. dry with materialdried over anhydrous MgSO4
  7. distillationThe solvent was distilled off
  8. customThe residue was purified by a silica gel column chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-85c6181e3c8f4cafa65f72c7cf39fe82
Source dataset
uspto-grants-1996_11
Patent number
US05576335

Reaction notes

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