Methylamine → 4-Methylaminomethyl-7-methoxycoumarin

HRID 1167050Notes

Reaction equation

HRID 1167050 reaction equation
[CH3:1][NH2:2].Br[CH2:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([O:15][CH3:16])=[CH:12][CH:13]=2)[O:8][C:7](=[O:17])[CH:6]=1.C(=O)([O-])[O-].[K+].[K+].ClCCl>O1CCCC1>[CH3:16][O:15][C:11]1[CH:10]=[C:9]2[C:14]([C:5]([CH2:4][NH:2][CH3:1])=[CH:6][C:7](=[O:17])[O:8]2)=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 6329MethylamineHCID 6344DichloromethaneHCID 11430Potassium Carbonate2×HCID 1218944-Bromomethyl-7-methoxycoumarin

Product 1

HCID 89318374-Methylaminomethyl-7-methoxycoumarin

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methylamine in tetrahydrofuran (2M, 1.10 ml) was added to an ice-cooled mixture of 4-bromomethyl-7-methoxycoumarin (0.30 g), potassium carbonate (0.5 g) and dichloromethane (10 ml). The mixture was stirred at room temperature for 2 days then added to an aqueous solution of potassium carbonate. The organic phase was washed with water, dried (MgSO4) and evaporated. The residue was purified by chromatography on silica gel (eluent 10% methanol in dichloromethane), then crystallised from methanol to give the title compound as a white solid (0.14 g).

Workup

  1. temperaturecooled
  2. washThe organic phase was washed with water
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue was purified by chromatography on silica gel (eluent 10% methanol in dichloromethane)
  6. customcrystallised from methanol

Sources & evidence

ORD record
ord-65df06f0f0ab4220954f09c98c2ae949
Source dataset
uspto-grants-2003_09
Patent number
US06617124B1

Reaction notes

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