Dimethylamine, hydrochloride → 7-Methoxy-4-(dimethylaminomethyl)coumarin

HRID 1167051Notes

Reaction equation

HRID 1167051 reaction equation
Cl.[CH3:2][NH:3][CH3:4].Br[CH2:6][C:7]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[O:10][C:9](=[O:19])[CH:8]=1.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[CH3:18][O:17][C:13]1[CH:12]=[C:11]2[C:16]([C:7]([CH2:6][N:3]([CH3:4])[CH3:2])=[CH:8][C:9](=[O:19])[O:10]2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 10473Dimethylamine, hydrochlorideHCID 11430Potassium CarbonateHCID 1218944-Bromomethyl-7-methoxycoumarin

Product 1

HCID 89318307-Methoxy-4-(dimethylaminomethyl)coumarinYield 55.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of dimethylamine hydrochloride (0.18 g), 4-bromomethyl-7-methoxycoumarin (0.30 g), potassium carbonate (0.5 g) and dichloromethane (10 ml) was stirred at room temperature for 2 days. The solid was filtered off and the filtrate concentrated. The residue was purified by chromatography on silica gel (eluent 5% methanol in dichloromethane), then crystallised from methanol to give the title compound as a white solid (0.145 g).

Workup

  1. filtrationThe solid was filtered off
  2. concentrationthe filtrate concentrated
  3. customThe residue was purified by chromatography on silica gel (eluent 5% methanol in dichloromethane)
  4. customcrystallised from methanol

Sources & evidence

ORD record
ord-375bfc90cbe34f90a54dbf2085e3f707
Source dataset
uspto-grants-2003_09
Patent number
US06617124B1

Reaction notes

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