Hydrochloric Acid → HCID 22625029, compound

HRID 279505Notes

Reaction equation

HRID 279505 reaction equation
C([O:4][C:5]1[CH:6]=[C:7]([CH:28]=[CH:29][C:30]=1[CH3:31])[NH:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:21][CH2:22][C:23]3[CH:27]=[CH:26][S:25][CH:24]=3)=[C:16]([O:19][CH3:20])[CH:17]=2)[N:12]=[CH:11][N:10]=1)(=O)C.[OH-].[Na+].[ClH:34]>C(Cl)Cl.CO.CO>[ClH:34].[OH:4][C:5]1[CH:6]=[C:7]([CH:28]=[CH:29][C:30]=1[CH3:31])[NH:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:21][CH2:22][C:23]3[CH:27]=[CH:26][S:25][CH:24]=3)=[C:16]([O:19][CH3:20])[CH:17]=2)[N:12]=[CH:11][N:10]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 226249964-(3-Acetoxy-4-methylanilino)-6-methoxy-7-(3-thienylmethoxy)quinazoline

Product 1

HCID 22625029HCID 22625029, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of 4-(3-acetoxy-4-methylanilino)-6-methoxy-7-(3-thienylmethoxy)quinazoline (200 mg, 0.45 mmol) in methylene chloride/methanol (1/1) (20 ml) was added, a 2M aqueous sodium hydroxide solution (0.67 ml, 1.35 mmol). The mixture was stirred for 35 minutes at ambient temperature, the solvents were evaporated, water was added to the residue and the solution was extracted with ethyl acetate. The organic layer was washed with water, brine, then dried (MgSO4) and evaporated to give a white solid. This solid was then dissolved into a saturated solution of hydrochloric acid in methanol (10 ml) and stirred for 10 minutes. The solid product was filtered and dried under a vacuum, to give 4-(3-hydroxy-4-methylanilino)-6-methoxy-7-(3-thienylmethoxy)quinazoline hydrochloride (127 mg, 66%).

Workup

  1. customthe solvents were evaporated
  2. additionwater was added to the residue
  3. extractionthe solution was extracted with ethyl acetate
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customto give a white solid
  8. stirringstirred for 10 minutes
  9. filtrationThe solid product was filtered
  10. customdried under a vacuum

Sources & evidence

ORD record
ord-9041b0658328488293c66d3c1d0b5b67
Source dataset
uspto-grants-2002_03
Patent number
US06362336B1

Reaction notes

Loading…