Isobutyraldehyde → 2,4-dimethyl-N-(2-methylpropyl)aniline

HRID 1746394Notes

Reaction equation

HRID 1746394 reaction equation
[CH:1](=O)[CH:2]([CH3:4])[CH3:3].[CH3:6][C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:8]=1[NH2:14].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCCC1>[CH3:6][C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:8]=1[NH:14][CH2:1][CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 6561IsobutyraldehydeHCID 72502,4-DimethylanilineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 284223892,4-dimethyl-N-(2-methylpropyl)aniline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Isobutyraldehyde (5 mL, 55.1 mmol) was added to (2,4-dimethylphenyl)amine (7.01 g, 57.8 mmol) in Tetrahydrofuran (50 mL) to give a brown solution. The solution was stirred for 20 mins at room temperature before sodium triacetoxy borohydride (16.34 g, 77 mmol) was added. The reaction mixture was stirred at room temperature for 18 hours and the reaction was analysed by LCMS to confirm conversion to the desired product. The solution was diluted with ethyl acetate (100 mL) and the organic phase washed with water (100 mL). The organic phase was separated from the aqueous phase using a separating funnel. The organic phase was concentrated in vacuo to give the product as a brown oil.

Workup

  1. customto give a brown solution
  2. additionwas added

Sources & evidence

ORD record
ord-937d620b7a4341b19ff066bcd0ffbbdd
Source dataset
uspto-grants-2015_10
Patent number
US09150508B2

Reaction notes

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