Methanol → 4-(3,4-Dihydroxybenzyl)amino-6,7,8-trimethoxyquinazoline hydrochloride

HRID 1900673Notes

Reaction equation

HRID 1900673 reaction equation
B(Cl)(Cl)[Cl:2].C1[O:31][C:30]2[CH:29]=[CH:28][C:9]([CH2:10][NH:11][C:12]3[C:21]4[C:16](=[C:17]([O:26][CH3:27])[C:18]([O:24][CH3:25])=[C:19]([O:22][CH3:23])[CH:20]=4)[N:15]=[CH:14][N:13]=3)=[CH:8][C:7]=2[O:6]1.CO>C(Cl)Cl.C(Cl)(Cl)Cl>[ClH:2].[OH:6][C:7]1[CH:8]=[C:9]([CH:28]=[CH:29][C:30]=1[OH:31])[CH2:10][NH:11][C:12]1[C:21]2[C:16](=[C:17]([O:26][CH3:27])[C:18]([O:24][CH3:25])=[C:19]([O:22][CH3:23])[CH:20]=2)[N:15]=[CH:14][N:13]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 25135Boron TrichlorideHCID 2059644-((3,4-(Methylenedioxy)benzyl)amino)-6,7,8-trimethoxyquinazoline

Product 1

HCID 187967434-(3,4-Dihydroxybenzyl)amino-6,7,8-trimethoxyquinazoline hydrochloride

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

30 ml of a 1.0M solution of boron trichloride in methylene chloride was dropped into a solution of 2.00 g (5.41 mmol) of 4-(3,4-methylenedioxybenzyl)amino-6,7,8-trimethoxyquinazoline in 150 ml of chloroform under stirring at room temperature. The obtained mixture was stirred at room temperature for 2 days, followed by the addition of methanol and the obtained mixture was distilled under a reduced pressure to remove the solvent. This procedure was repeated thrice and the obtained residue was purified by silica gel column chromatography (chloroform/n-hexane). Hydrochloric acid/ethanol was added to the eluate and the obtained mixture was distilled under a reduced pressure to remove the solvent, followed by the addition of ethanol. The crystals thus formed were recovered by filtration. Thus, 0.59 g of the title compound was obtained as a colorless needle.

Workup

  1. stirringThe obtained mixture was stirred at room temperature for 2 days
  2. distillationthe obtained mixture was distilled under a reduced pressure
  3. customto remove the solvent
  4. customthe obtained residue was purified by silica gel column chromatography (chloroform/n-hexane)
  5. additionHydrochloric acid/ethanol was added to the eluate
  6. distillationthe obtained mixture was distilled under a reduced pressure
  7. customto remove the solvent
  8. additionfollowed by the addition of ethanol
  9. customThe crystals thus formed
  10. filtrationwere recovered by filtration

Sources & evidence

ORD record
ord-e35fd79631004756be87527bde643883
Source dataset
uspto-grants-1996_11
Patent number
US05576322

Reaction notes

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