Acetaldehyde → 2-METHYL-4-NITRO-N,N-DIETHYLANILINE

HRID 450094Notes

Reaction equation

HRID 450094 reaction equation
S(=O)(=O)(O)O.[CH:6](=O)[CH3:7].[CH3:9][C:10]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[CH:13][C:11]=1[NH2:12].[BH4-].[Na+].C(=O)([O-])[O-].[Na+].[Na+].[CH2:28]1COC[CH2:29]1>O>[CH2:28]([N:12]([CH2:6][CH3:7])[C:11]1[CH:13]=[CH:14][C:15]([N+:17]([O-:19])=[O:18])=[CH:16][C:10]=1[CH3:9])[CH3:29]

Participants

8

Reactant 6

HCID 177AcetaldehydeHCID 1118Sulfuric AcidHCID 74412-Methyl-4-nitroanilineHCID 8028Tetrahydrofuran2×HCID 10340Sodium CarbonateHCID 4311764Sodium borohydride

Product 1

HCID 116298342-METHYL-4-NITRO-N,N-DIETHYLANILINEYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3N Sulfuric acid (20 ml) was added dropwise to a stirred solution of 20% acetaldehyde (10 ml, 45.45 mmol) in THF (10 ml) at 0° C. After 15 min, this mixture was added to a solution of 2-methyl-4-nitro aniline (1 g, 6.6 mmol) in THF (10 ml). Sodium borohydride (1.5 g, 40.5 mmol) was added portion-wise and the reaction mixture was stirred at room temperature for 2 hr. The reaction mixture was then diluted with water (60 ml), basified with sodium carbonate, and extracted with ethyl acetate. The organic layer was washed with water, brine and dried. Evaporation to dryness gave a residue, which was chromatographed over silica gel using 0-3% ethyl acetate in pet ether to give diethyl-(2-methyl-4-nitro-phenyl)-amine (720 mg, 50%) as oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water, brine
  3. customdried
  4. customEvaporation to dryness
  5. customgave a residue, which
  6. customwas chromatographed over silica gel using 0-3% ethyl acetate in pet ether

Sources & evidence

ORD record
ord-3d10203e2cf94cc391a94b4c5d5bdbb3
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

Loading…