4-(3-Acetoxy-4-methylanilino)-7-benzyloxy-6-methoxyquinazoline hydrochloride → 4-(3-Acetoxy-4-methylanilino)-7-hydroxy-6-methoxyquinazoline hydrochloride

HRID 279498Notes

Reaction equation

HRID 279498 reaction equation
[ClH:1].[C:2]([O:5][C:6]1[CH:7]=[C:8]([CH:30]=[CH:31][C:32]=1[CH3:33])[NH:9][C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:22]CC3C=CC=CC=3)=[C:17]([O:20][CH3:21])[CH:18]=2)[N:13]=[CH:12][N:11]=1)(=[O:4])[CH3:3]>[Pd].CO.CN(C=O)C.ClC(Cl)Cl>[ClH:1].[C:2]([O:5][C:6]1[CH:7]=[C:8]([CH:30]=[CH:31][C:32]=1[CH3:33])[NH:9][C:10]1[C:19]2[C:14](=[CH:15][C:16]([OH:22])=[C:17]([O:20][CH3:21])[CH:18]=2)[N:13]=[CH:12][N:11]=1)(=[O:4])[CH3:3]

Participants

6

Reactant 1

HCID 226250264-(3-Acetoxy-4-methylanilino)-7-benzyloxy-6-methoxyquinazoline hydrochloride

Product 1

HCID 1356711804-(3-Acetoxy-4-methylanilino)-7-hydroxy-6-methoxyquinazoline hydrochlorideYield 100%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(3-acetoxy-4-methylanilino)-7-benzyloxy-6-methoxyquinazoline hydrochloride (2.68 g, 5.75 mmol), 10% palladium-on-charcoal catalyst (0.27 g) in methanol (50 ml), DMF (12 ml) and trichloromethane (50 ml) was stirred at ambient temperature under an atmosphere of hydrogen (1.5 atmospheres) for 30 minutes. The catalyst was filtered off and the filtrate evaporated. The residual solid was triturated in ether, filtered off and dried under vacuum at 50° C. to give 4-(3-acetoxy-4-methylanilino)-7-hydroxy-6-methoxyquinazoline hydrochloride (2.1 g, 100%).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate evaporated
  3. customThe residual solid was triturated in ether
  4. filtrationfiltered off
  5. customdried under vacuum at 50° C.

Sources & evidence

ORD record
ord-f79b56689d0d40bf993f7ae89d50579f
Source dataset
uspto-grants-2002_03
Patent number
US06362336B1

Reaction notes

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