Ethanol → Para-aminobenzylidenecamphor

HRID 2254510Notes

Reaction equation

HRID 2254510 reaction equation
C(O)C.[Cl-].[NH4+].[N+:6]([C:9]1[CH:26]=[CH:25][C:12]([CH:13]=[C:14]2[CH:19]3[C:20]([CH3:22])([CH3:21])[C:16]([CH3:23])([CH2:17][CH2:18]3)[C:15]2=[O:24])=[CH:11][CH:10]=1)([O-])=O>[Zn].O>[NH2:6][C:9]1[CH:10]=[CH:11][C:12]([CH:13]=[C:14]2[CH:19]3[C:20]([CH3:22])([CH3:21])[C:16]([CH3:23])([CH2:17][CH2:18]3)[C:15]2=[O:24])=[CH:25][CH:26]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 67855243Paranitrobenzylidenecamphor

Product 1

HCID 68878284Para-aminobenzylidenecamphorYield 99%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Procedure

A mixture of fine zinc powder (60 g), ethanol (250 ml), ammonium chloride (2 g) and water (20 ml) is heated to the reflux temperature and the paranitrobenzylidenecamphor (20 g, 0.07 mol) is added in portions with stirring. The mixture is allowed to reflux for half an hour, the zinc is filtered and the mixture is rinsed with alcohol. The filtrate is poured in ice (500 g). The precipitate obtained is filtered, washed with water and dried under vacuum. A quantitative yield of para-aminobenzylidenecamphor (17.7 g) is obtained. It is recrystallised in ethanol to give the expected derivative:

Workup

  1. temperatureis heated to the reflux temperature
  2. temperatureto reflux for half an hour
  3. filtrationthe zinc is filtered
  4. washthe mixture is rinsed with alcohol
  5. additionThe filtrate is poured in ice (500 g)
  6. customThe precipitate obtained
  7. filtrationis filtered
  8. washwashed with water
  9. customdried under vacuum

Sources & evidence

ORD record
ord-bb1ad6f0bc584841b2b0836efcb78d68
Source dataset
uspto-grants-1993_08
Patent number
US05236698

Reaction notes

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