tert-Butoxy bis(dimethylamino)methane → [2-(2-Chloro-6-methoxyquinolin-4-yl)ethenyl]dimethylamine

HRID 725884Notes

Reaction equation

HRID 725884 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([CH3:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:13][CH3:14])[CH:8]=2)[N:3]=1.C(O[CH:20](N(C)C)[N:21]([CH3:23])[CH3:22])(C)(C)C>>[Cl:1][C:2]1[CH:11]=[C:10]([CH:12]=[CH:20][N:21]([CH3:23])[CH3:22])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:13][CH3:14])[CH:8]=2)[N:3]=1

Participants

3

Reactant 2

HCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 2247882-Chloro-6-methoxy-4-methylquinoline

Product 1

HCID 53676043[2-(2-Chloro-6-methoxyquinolin-4-yl)ethenyl]dimethylamineYield 92.6%

Conditions

Temperature
120 °C

Procedure

2-Chloro-6-methoxy-4-methylquinoline (25 g, 0.12 mol) and tert-butoxybis(dimethylamino)methane (Bredereck's reagent) (30 g, 0.17 mol) was stirred under heating at 120° C. for 1.5 hours. After cooling the reaction mixture, the precipitated crystals were washed with diisopropyl ether to obtain the title compound (29.2 g, 92%).

Workup

  1. temperatureAfter cooling the reaction mixture
  2. washthe precipitated crystals were washed with diisopropyl ether

Sources & evidence

ORD record
ord-028b9fadd9ed40c7aa6cd3c86c81a0b0
Source dataset
uspto-grants-1998_01
Patent number
US05708005

Reaction notes

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