Methanol → 3-[(Dimethylamino)methyl]benzaldehyde

HRID 1107725Notes

Reaction equation

HRID 1107725 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[C:11]([C:13]1[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=1)[CH2:16][N:17]([CH3:19])[CH3:18])#N.C[OH:24].[OH-].[Na+]>C1(C)C=CC=CC=1.CO.O>[CH3:18][N:17]([CH2:16][C:15]1[CH:14]=[C:13]([CH:22]=[CH:21][CH:20]=1)[CH:11]=[O:24])[CH3:19]

Participants

7

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 46410883-(dimethylaminomethyl)benzonitrileHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 145948463-[(Dimethylamino)methyl]benzaldehyde

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

Diisobutylaluminium hydride (1.0M solution in toluene, 20 ml, 20 mmol) was added dropwise to a solution of 3-cyano-(N,N-dimethyl)benzylamine [Example K(a)] (3.20 g, 20 mmol) in toluene (50 ml). The mixture was stirred at room temperature for 2 h., methanol (30 ml) was cautiously added, followed by methanol/water (1:1, 40 ml) and 10% aqueous sodium hydroxide (100 ml). The mixture was extracted twice with diethyl ether, washed with saturated aqueous sodium chloride, dried over sodium sulphate and evaporated to give a yellow oil (3.0 g). M+ 163; 360 MHz 1H n.m.r (CDCl3) 10.02 (1H, s), 7.83 (1H, s), 7.79 (1H, d, J 7.6 Hz), 7.60 (1H, d, J 7.5 Hz), 7.49 (1H, t, J 7.5 Hz), 3.50 (2H, ), 2.26 (6H, s).

Workup

  1. extractionThe mixture was extracted twice with diethyl ether
  2. washwashed with saturated aqueous sodium chloride
  3. dry with materialdried over sodium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-98b4331acce24dfb84d6051e54254f38
Source dataset
uspto-grants-2000_05
Patent number
US06063789

Reaction notes

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