Ethanol → 3-(2,6-Dimethylphenyl)propan-1-amine

HRID 4768Notes

Reaction equation

HRID 4768 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[CH2:9][CH2:10][CH2:11][N:12]1C(=O)C2C(=CC=CC=2)C1=O.C(O)C.NN>>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[CH2:9][CH2:10][CH2:11][NH2:12]

Participants

4

Reactant 3

HCID 702EthanolHCID 9321HydrazineHCID 136567382-[3-(2,6-dimethylphenyl)propyl]-1H-isoindole-1,3(2H)-dione

Product 1

HCID 201519293-(2,6-Dimethylphenyl)propan-1-amineYield 59%

Procedure

A 10 g (34.4 mmole) sample of the title compound of Example 33 was refluxed for 2 hours in 150 ml of ethanol containing 1.2 g (36.7 mmole) of 97% hydrazine. After concentrating the solution, the white crystalline residue was mixed with 100 ml of 10% NaOH and 100 ml of ether. The aqueous phase was separated and extracted with another 100 ml portion of ether. The combined ether extracts were than washed with water, dried over MgSO4 and stripped of all solvent under reduced pressure to yield 3.3 g (59%) of the product as an oil. This material was used without further purification.

Workup

  1. concentrationAfter concentrating the solution
  2. additionthe white crystalline residue was mixed with 100 ml of 10% NaOH and 100 ml of ether
  3. customThe aqueous phase was separated
  4. extractionextracted with another 100 ml portion of ether
  5. washthan washed with water
  6. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-59ee8f90580b491d9685262ca4315869
Source dataset
uspto-grants-1988_02
Patent number
US04727189

Reaction notes

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