Hydrochloric Acid → 2,6-Dimethylbenzylamine

HRID 450889Notes

Reaction equation

HRID 450889 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-97fc6d432f4c42c39db4e1e86c19e87d
Source dataset
uspto-grants-2013_07
Patent number
US08487000B2

Reaction notes

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