Ethanol → HCID 20144501, compound

HRID 649043Notes

Reaction equation

HRID 649043 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[C:7]([Cl:13])[C:8]([OH:12])=[CH:9][CH:10]=2)[O:5][C:4](=[O:14])[CH:3]=1.[CH2:15](O)[CH3:16].[CH2:18]([NH:20][CH2:21]C)[CH3:19].C=O>C(Cl)(Cl)Cl>[CH3:1][C:2]1[C:11]2[C:6](=[C:7]([Cl:13])[C:8]([OH:12])=[C:9]([CH2:21][N:20]([CH2:15][CH3:16])[CH2:18][CH3:19])[CH:10]=2)[O:5][C:4](=[O:14])[CH:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 712FormaldehydeHCID 8021DiethylamineHCID 20144512HCID 20144512, compound

Product 1

HCID 20144501HCID 20144501, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

21 g of 4-methyl-7-hydroxy-8-chlorocoumarin are mixed with 180 ml of ethanol, 20 ml of chloroform, 9.5 of of diethylamine and 11.2 g of 35% aqueous formaldehyde solution. The mixture is refluxed for 20 hours, being kept in constant agitation meanwhile; the ethanol and chloroform are evaporated in vacuum. The residue is solubilized in the methylenechloride-ethyl acetate-methanol mixture (7+3+1) and the solution is used for a chromatographic separation on silica, eluting with the same mixture of solvents. 4-methyl-6-diethylaminomethyl-7-hydroxy-8-chlorocoumarin is thus obtained. It is then treated with ethyl acetate and then, by adding gaseous hydrochloric acid, crystalline hydrochloride is formed. The precipitate is separated and crystallized from ethyl acetate. After filtering and drying the crystals, hydrochloride of 4-methyl-6-diethylaminomethyl-7-hydroxy-8-chlorocoumarin is obtained.

Workup

  1. temperatureThe mixture is refluxed for 20 hours
  2. customthe ethanol and chloroform are evaporated in vacuum
  3. customthe solution is used for a chromatographic separation on silica
  4. washeluting with the same mixture of solvents

Sources & evidence

ORD record
ord-18fe0a073c3c4bc1abd1f40290875388
Source dataset
uspto-grants-1988_04
Patent number
US04737517

Reaction notes

Loading…