Dimethylamine → HCID 22282638, compound

HRID 1370337Notes

Reaction equation

HRID 1370337 reaction equation
Br[C:2]1[CH:11]=[C:10]([Br:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:13][NH:14][CH3:15]>CCO>[Br:12][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]([N:14]([CH3:15])[CH3:13])[CH:11]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 8246082,4-dibromoquinoline

Product 1

HCID 22282638HCID 22282638, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2,4-dibromoquinoline (273 mg, 1.0 mmol) in EtOH (15 mL) was treated with aqueous dimethylamine (40%, 0.4 mL, 3 mmol), stirred at room temperature for 16 h, concentrated in vacuo and purified by chromatography [SiO2; heptane-EtOAc (9:1)] to give the product (119 mg, 50%) as a cream solid: IR νmax (Nujol)/cm−1 2924, 2854, 1598, 1546, 1510, 1463, 1379 and 754; NMR δH (400 MHz, CDCl3) 3.21 (6H, s), 7.21 (1H, s), 7.23-7.26 (1H, m), 7.55 (1H, t, J 8.2 Hz), 7.68 (1H, d, J 8.5 Hz) and 7.94 (1H, d, J 7.1 Hz); M/Z 251 (M+H)+.

Workup

  1. concentrationconcentrated in vacuo
  2. custompurified by chromatography [SiO2; heptane-EtOAc (9:1)]

Sources & evidence

ORD record
ord-d68cbca7fb61459bb6647eab92a2ebfe
Source dataset
uspto-grants-2003_06
Patent number
US06583156B1

Reaction notes

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