Water → 4-Bromo-N,N-dibenzyl-2-quinolineamine

HRID 1370338Notes

Reaction equation

HRID 1370338 reaction equation
[NH2:1][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.[H-].[Na+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>C1COCC1>[Br:12][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]([N:1]([CH2:10][C:9]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 140674194-Bromoquinolin-2-amine

Product 1

HCID 185114254-Bromo-N,N-dibenzyl-2-quinolineamineYield 185.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-amino-4-bromoquinoline (244 mg, 1.09 mmol) in THF (5 mL) at 0° C. was treated with NaH (96 mg, 60% dispersion in oil, 2.4 mmol), stirred for 30 min, treated with benzyl bromide (0.335 mL, 2.4 mmol), stirred at room temperature for 3 days, poured into water (30 mL), extracted with EtOAc (2×10 mL), dried (MgSO4), concentrated in vacuo, purified by chromatography [SiO2; heptane-EtOAc (10:1)] and the resulting solid recystallised (MeOH) to give the product (407 mg, 99%) as a white crystalline solid: IR νmax (Nujol)/cm−1 3059, 3020, 2955, 2925, 2854, 1609, 1592, 1542, 1498, 1455, 1426 and 1358; NMR δH (400 MHz, CDCl3) 4.89 (4H, s), 7.15 (1H, s), 7.20-7.68 (11H, m),7.56 (1H, t, J 7.0 Hz), 7.69 (1H, d, J 8.7 Hz) and 7.94 (1H, d, J 8.4 Hz).

Workup

  1. stirringstirred at room temperature for 3 days
  2. extractionextracted with EtOAc (2×10 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. custompurified by chromatography [SiO2; heptane-EtOAc (10:1)]

Sources & evidence

ORD record
ord-239c4d52696947ce9944ae9066d05d90
Source dataset
uspto-grants-2003_06
Patent number
US06583156B1

Reaction notes

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