Acetic Acid → N-(1-ethylpropyl)-3,4-dimethylaniline

HRID 1111880Notes

Reaction equation

HRID 1111880 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([CH3:9])[CH:3]=1.[CH2:10]([C:12]([CH2:14][CH3:15])=O)[CH3:11].C([BH3-])#N.[Na+].C(O)(=O)C>CO>[CH2:10]([CH:12]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([CH3:9])[CH:3]=1)[CH2:14][CH3:15])[CH3:11]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 72483,4-DimethylanilineHCID 7288Ethyl ketoneHCID 5003444Sodium cyanoborohydride

Product 1

HCID 91984N-(1-ethylpropyl)-3,4-dimethylanilineYield 97.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3,4-xylidine (1.2 g., 0.01 mole) and diethyl ketone (5 ml.) in methanol (20 ml.) is stirred at room temperature in the presence of sodium cyanoborohydride (1.1 g.) and 3A molecular sieves (3.0 g.). The pH is monitored each half hour and maintained at 6 by adding acetic acid in 5 drop portions as required. After 7 hours, the sieves are removed by filtration and the filtrate is diluted with water (100 ml.) and then acidified with hydrochloric acid. The solution is then basified with solid potassium carbonate and extracted with ethyl ether. The ether solution is dried and then evaporated leaving the desired product as a residual oil in 97.5% yield and in 93% purity as determined by gas-liquid chromatography. The compound had a boiling point of 80° C. at a pressure of 0.1 mm. Its elemental analysis is as follows:

Workup

  1. temperaturemaintained at 6
  2. waitAfter 7 hours
  3. customthe sieves are removed by filtration
  4. additionthe filtrate is diluted with water (100 ml.)
  5. extractionextracted with ethyl ether
  6. dry with materialThe ether solution is dried
  7. customevaporated

Sources & evidence

ORD record
ord-429832637d804aeaa090bbcde588d6eb
Source dataset
uspto-grants-1978_10
Patent number
US04119669

Reaction notes

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