Salicylaldehyde → 2-[3-(Dimethylamino)propoxy]benzaldehyde

HRID 918208Notes

Reaction equation

HRID 918208 reaction equation
[CH:1](=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[H-].[Na+].[CH3:12][N:13]([CH3:18])[CH2:14][CH2:15][CH2:16]Cl>C1(C)C=CC=CC=1>[CH3:12][N:13]([CH3:18])[CH2:14][CH2:15][CH2:16][O:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[CH:1]=[O:9]

Participants

5

Reactant 3

HCID 6998SalicylaldehydeHCID 24758Sodium hydrideHCID 669603-Chloro-N,N-dimethyl-1-propanamine

Product 1

HCID 29959682-[3-(Dimethylamino)propoxy]benzaldehydeYield 77%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The reaction between 100 g (0.82 mole) of salicylaldehyde, 40 g (0.82 mole) of 50% NaH, and 650 ml (1.2 mole) of 1.89 N 3-dimethylaminopropyl chloride in toluene in a procedure described in Example 2, part A, gives 130.4 g (77%) of yellow product, bp 125°-130°/0.5 mm.

Sources & evidence

ORD record
ord-3d5a34b24ce640f4817b49fcde70cc04
Source dataset
uspto-grants-1976_07
Patent number
US03969527

Reaction notes

Loading…