Diethyl Ether → 2-Chloro-6-methylbenzylamine

HRID 328624

Reaction equation

HRID 328624 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].CCOCC.[C:12]([C:14]1[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:21])#[N:13].C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>O>[Cl:20][C:19]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:21])[C:14]=1[CH2:12][NH2:13]

Participants

6

Reactant 4

HCID 3283Diethyl Ether2×HCID 230532-Chloro-6-methylbenzonitrileHCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydride

Product 1

HCID 5217992-Chloro-6-methylbenzylamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred mixture of 5.7 parts of lithium aluminum hydride in 20 parts of ether is added dropwise a solution of 15 parts of 2-cyano-3-chlorotoluene in 140 parts of ether at reflux temperature. After the addition is complete, stirring at reflux temperature is continued for one hour. The reaction mixture is cooled in an ice-bath and decomposed with 25 parts of water and with a 20% solution of potassium-sodium tartrate (450 parts). The aqueous phase is separated and extracted with ether. The combined ether layers are washed with water, dried, filtered and evaporated. The oily residue is distilled in vacuo, yielding 12 parts of 2-chloro-6-methylbenzylamine; bp. 113° -118° C at 18 mm. pressure.

Workup

  1. temperatureat reflux temperature
  2. additionAfter the addition
  3. temperatureat reflux temperature
  4. temperatureThe reaction mixture is cooled in an ice-bath
  5. customThe aqueous phase is separated
  6. extractionextracted with ether
  7. washThe combined ether layers are washed with water
  8. customdried
  9. filtrationfiltered
  10. customevaporated
  11. distillationThe oily residue is distilled in vacuo

Sources & evidence

ORD record
ord-dd187b8bf2c34f448005bd73d6e879f0
Source dataset
uspto-grants-1977_04
Patent number
US04017631

Linked notes

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