Acetone → N-Isopropyl-2,3-xylidine

HRID 2397351Notes

Reaction equation

HRID 2397351 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[CH3:9].[CH3:10][C:11]([CH3:13])=O.[BH4-].[Na+]>CO>[CH:11]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[CH3:9])([CH3:13])[CH3:10]

Participants

5

Reactant 3

HCID 180AcetoneHCID 68932,3-DimethylanilineHCID 4311764Sodium borohydride

Product 1

HCID 6454512N-Isopropyl-2,3-xylidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 12 g of 2,3-xylidine, 60 ml of acetone and 30 g of type 5A sieves (alumino silicate) are placed in a flask and stirred overnight at room temperature. The mixture is filtered and the filtrate concentrated in vacuo to yield an oily residue. This residue is taken up in 100 ml of methanol, treated with 4.0 g of sodium borohydride and warmed to above 15° C. The mixture is made acidic, then basic, and finally extracted with ether to yield 11.4 g of N-isopropyl-2,3-xylidine which is verified by infra-red spectra and NMR.

Workup

  1. customare placed in a flask
  2. filtrationThe mixture is filtered
  3. concentrationthe filtrate concentrated in vacuo
  4. customto yield an oily residue
  5. temperaturewarmed to above 15° C
  6. extractionbasic, and finally extracted with ether

Sources & evidence

ORD record
ord-ee2e2749ac4746828c04221a19987cfd
Source dataset
uspto-grants-1977_05
Patent number
US04021483

Reaction notes

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