Hydrochloric Acid → 4-(2-Fluoro-5-hydroxy-4-methylanilino)-7-methoxyacetamidoquinazoline hydrochloride

HRID 634722Notes

Reaction equation

HRID 634722 reaction equation
[F:1][C:2]1[CH:24]=[C:23]([CH3:25])[C:22]([O:26]C(OC)=O)=[CH:21][C:3]=1[NH:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([NH:15][C:16](=[O:20])[CH2:17][O:18][CH3:19])=[CH:12][CH:13]=2)[N:8]=[CH:7][N:6]=1.[ClH:31]>CO.[OH-].[Na+].O>[ClH:31].[F:1][C:2]1[CH:24]=[C:23]([CH3:25])[C:22]([OH:26])=[CH:21][C:3]=1[NH:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([NH:15][C:16](=[O:20])[CH2:17][O:18][CH3:19])=[CH:12][CH:13]=2)[N:8]=[CH:7][N:6]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 212603364-(2-Fluoro-5-methoxycarbonyloxy-4-methylanilino)-7-methoxyacetamidoquinazoline

Product 1

HCID 212603614-(2-Fluoro-5-hydroxy-4-methylanilino)-7-methoxyacetamidoquinazoline hydrochlorideYield 36%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 4-(2-fluoro-5-methoxycarbonyloxy-4-methylanilino)-7-methoxyacetamidoquinazoline (201 mg, 0.5mmol) in methanol (5 ml) and 2M aqueous sodium hydroxide solution (0.5 ml) was stirred at ambient temperature for 1 hour. The mixture was diluted with water and adjusted to pH6 with 2M hydrochloric acid. The precipitated solid was collected by filtration, washed with water, dried and then dissolved in a mixture of methylene chloride and methanol. A 5M solution of hydrogen chloride in isopropanol (0.3 ml) was added and most of the solvent removed by evaporation. The precipitated solid was collected by filtration, washed with methylene chloride and dried under vacuum to give 4-(2-fluoro-5-hydroxy-4-methylanilino)-7-methoxyacetamidoquinazoline hydrochloride (70 mg, 36%) as a yellow solid.

Workup

  1. filtrationThe precipitated solid was collected by filtration
  2. washwashed with water
  3. customdried
  4. dissolutiondissolved in a mixture of methylene chloride and methanol
  5. additionA 5M solution of hydrogen chloride in isopropanol (0.3 ml) was added and most of the solvent
  6. customremoved by evaporation
  7. filtrationThe precipitated solid was collected by filtration
  8. washwashed with methylene chloride
  9. customdried under vacuum

Sources & evidence

ORD record
ord-026774a3a16f4150b96ba9a6dade2e23
Source dataset
uspto-grants-2001_02
Patent number
US06184225B2

Reaction notes

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