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

HRID 1737464Notes

Reaction equation

HRID 1737464 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-b781504450c346d4af9efb79be187f2d
Source dataset
uspto-grants-1999_10
Patent number
US05962458

Reaction notes

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