Hydrochloric Acid → 2,6-Dimethylbenzylamine

HRID 2262800Notes

Reaction equation

HRID 2262800 reaction equation
[CH3:1][C:2]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:3]=1[CH2:4][N:5]1C(=O)C2=CC=CC=C2C1=O.O.NN.Cl.O>C(O)C>[CH3:1][C:2]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:3]=1[CH2:4][NH2:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 10825581N-(2,6-Dimethylbenzyl)phthalimide

Product 1

HCID 126229122,6-Dimethylbenzylamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of N-(2,6-Dimethylbenzyl)phthalimide (Step B, 7.77 g, 29.3 mmol) in ethanol (80 ml) was added hydrazine monohydrate (2.16 ml, 44.52 mmol) and the reaction mixture was refluxed for 3.5 hours. To this reaction mixture was added c HCl to bring pH to 1 and refluxing continued for another 3.5 hours, water was added and reaction mixture was filtered, the filtrate was concentrated and pH was adjusted to 10 with 2 N NaOH. The residue was taken in methylene chloride and washed with brine, dried over Na2SO4, filtered and concentrated to give an oil which was used without further purification.

Workup

  1. temperaturethe reaction mixture was refluxed for 3.5 hours
  2. temperaturerefluxing
  3. customreaction mixture
  4. filtrationwas filtered
  5. concentrationthe filtrate was concentrated
  6. washwashed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give an oil which
  11. customwas used without further purification

Sources & evidence

ORD record
ord-6def8b822cb14d1bbe5435a8365cb5e7
Source dataset
uspto-grants-2010_12
Patent number
US07851494B2

Reaction notes

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