Dimethylformamide → N-(2-(dimethylamino)ethyl)-3-(6-formyl-3,4-dihydroquinolin-1(2H)-yl)propanamide

HRID 1810949Notes

Reaction equation

HRID 1810949 reaction equation
[N:1]1([CH2:11][CH2:12][C:13]([NH:15][CH2:16][CH2:17][N:18]([CH3:20])[CH3:19])=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.O=P(Cl)(Cl)Cl.CN([CH:29]=[O:30])C>>[CH3:20][N:18]([CH3:19])[CH2:17][CH2:16][NH:15][C:13](=[O:14])[CH2:12][CH2:11][N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH:29]=[O:30])=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 592379773-(3,4-dihydroquinolin-1(2H)-yl)-N-(2-(dimethylamino)ethyl) propanamide

Product 1

HCID 59237984N-(2-(dimethylamino)ethyl)-3-(6-formyl-3,4-dihydroquinolin-1(2H)-yl)propanamide

Procedure

The procedure was carried out as described previously in step (a) of Example 5 with Compound 8 (0.74 g, 2.7 mmol), POCl3 (506 μL, 5.4 mmol), and DMF (8.6 mL). Compound 9 was obtained (0.31 g) as a viscous yellow liquid and used without any further purification. The structure of Compound 9 is given below:

Sources & evidence

ORD record
ord-a807ded32c6749c697e5a3c5c47d87de
Source dataset
uspto-grants-2013_01
Patent number
US08362250B2

Reaction notes

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