Methylamine → (8-Bromo-quinolin-2-ylmethyl)-methylamine

HRID 499980Notes

Reaction equation

HRID 499980 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH2:12]Br)[CH:8]=[CH:7]2.[CH3:14][NH2:15]>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH2:12][NH:15][CH3:14])[CH:8]=[CH:7]2

Participants

4

Reactant 2

HCID 6329MethylamineHCID 574568018-Bromo-2-(bromomethyl)quinoline

Product 1

HCID 59012643(8-Bromo-quinolin-2-ylmethyl)-methylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3 (1 g, 3.32 mmol) in THF (5 mL) was added methylamine (10.5 mL of 40% water solution). The solution was stirred for 30 min and then extracted with EtOAc (30 mL). The organic phase was washed with DI water (2×20 mL), dried and concentrated to give a red oil. Purification by chromatography (MeOH/DCM 1:99) yielded yellow solid.(0.8 g, 96%) 1H NMR (400 MHz CDCl3) δ8.09 (1H, d, J=8.4 Hz), 8.02 (1H, d, J=7.2 Hz), 7.77 (1H, d, J=8 Hz), 7.49 (1H, d, J=8.4 Hz), 7.36 (1H, t, J=8.0 Hz), 4.12 (2H, s), 2.58 (3H, s).

Workup

  1. extractionextracted with EtOAc (30 mL)
  2. washThe organic phase was washed with DI water (2×20 mL)
  3. customdried
  4. concentrationconcentrated
  5. customto give a red oil
  6. customPurification by chromatography (MeOH/DCM 1:99)
  7. customyielded yellow solid

Sources & evidence

ORD record
ord-f9c44caed23747f9805e843f1dda4502
Source dataset
uspto-grants-2010_08
Patent number
US07767817B2

Reaction notes

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