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

HRID 1420892Notes

Reaction equation

HRID 1420892 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-35e9e25248f7473a8cf4f7384276b4ac
Source dataset
uspto-grants-2000_06
Patent number
US06071921

Reaction notes

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