Formaldehyde → N,N-Dimethylaniline

HRID 545496Notes

Reaction equation

HRID 545496 reaction equation
C([BH3-])#N.[Na+].[C:5](#N)[CH3:6].[CH3:8][N:9]([CH3:12])[CH:10]=O.C=O.O1C[CH2:18][CH2:17][CH2:16]1>>[CH3:8][N:9]([CH3:12])[C:10]1[CH:6]=[CH:5][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 5

HCID 712FormaldehydeHCID 6228DimethylformamideHCID 6342AcetonitrileHCID 8028TetrahydrofuranHCID 5003444Sodium cyanoborohydride

Product 1

HCID 949N,N-Dimethylaniline

Procedure

Alternatively the reduction can be accomplished with sodium cyanoborohydride in an inert solvent such as acetonitrile, dimethylformamide, or tetrahydrofuran. An alkyl aldehyde such as formaldehyde can be used in excess to obtain a dimethyl aniline of formula (24) (R5 and R6 each represent methyl). The reaction is accomplished at room temperture to the reflux temperature of the solvent for about 4 to 48 hours. The product can be isolated by common extractive techniques and purified by silica gel chromatography.

Sources & evidence

ORD record
ord-9d927092c13d4f1f84e16dc6d5a33423
Source dataset
uspto-grants-2011_05
Patent number
US07935722B2

Reaction notes

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