Dimethylformamide → 4-(2-(Dimethylamino)ethyl)benzaldehyde

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]([CH3:12])[CH3:11])=[CH:4][CH:3]=1.[Mg].CN([CH:17]=[O:18])C>>[CH3:11][N:10]([CH3:12])[CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([CH:17]=[O:18])=[CH:3][CH:4]=1

Participants

Reactant 3

HCID 6228Dimethylformamide

HCID 5462224Magnesium

HCID 10751802(2-(4-Bromophenyl)ethyl)dimethylamine

Product 1

HCID 217040524-(2-(Dimethylamino)ethyl)benzaldehyde

Procedure

2-(4-Bromophenyl)-N,N-dimethylethylamine (6.8 g) was refluxed under heating with magnesium for 1 hr to prepare a Grignard reagent, which was reacted with DMF to give the objective 4-(2-dimethylaminoethyl)benzaldehyde as an oil (4.2 g).

Sources & evidence

ORD record: ord-3829d2f2230f418abd08f4b1fb067420
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06288061B1

Reaction notes

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