Hydrochloric Acid → HCID 22625029, compound

HRID 1384521Notes

Reaction equation

HRID 1384521 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%). m.p. 246-248° C. 1H NMR Spectrum: (DMSOd6) 2.15(s, 3H); 3.98(s, 3H); 5.32(s, 2H); 6.98(dd, 1H); 7.10(s, 1H); 7.14(d, 1H); 7.25(d, 1H); 7.40(s, 1H); 7.61(dd, 1H); 7.70(d, 1H); 8.12(s, 1H); 8.74(s, 1 H); 9.60(s, 1H) MS−ESI: 394 [MH]+

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-d769dabb3f6e407fb98158398ff30585
Source dataset
uspto-grants-2001_07
Patent number
US06258951B1

Reaction notes

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