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

HRID 279497Notes

Reaction equation

HRID 279497 reaction equation
Cl.[CH2:2]([O:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([Cl:20])=[N:15][CH:16]=[N:17]2)=[CH:12][C:11]=1[O:21][CH3:22])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:23]([O:26][C:27]1[CH:28]=[C:29]([CH:31]=[CH:32][C:33]=1[CH3:34])[NH2:30])(=[O:25])[CH3:24]>C(O)(C)C>[ClH:20].[C:23]([O:26][C:27]1[CH:28]=[C:29]([CH:31]=[CH:32][C:33]=1[CH3:34])[NH:30][C:14]1[C:13]2[C:18](=[CH:19][C:10]([O:9][CH2:2][C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)=[C:11]([O:21][CH3:22])[CH:12]=2)[N:17]=[CH:16][N:15]=1)(=[O:25])[CH3:24]

Participants

4

Reactant 2

HCID 220308367-(Benzyloxy)-4-chloro-6-methoxyquinazoline hydrochlorideHCID 224783113-Acetoxy-4-methylaniline

Product 1

HCID 226250264-(3-Acetoxy-4-methylanilino)-7-benzyloxy-6-methoxyquinazoline hydrochlorideYield 89.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 7-benzyloxy-4-chloro-6-methoxyquinazoline hydrochloride (2.18 g, 6.47 mmol), 3-acetoxy-4-methylaniline (1.32 g, 8 mmol) and isopropanol (50 ml) was stirred and heated at reflux for 1 hour. The mixture was cooled to ambient temperature. The precipitate was filtered off, washed with isopropanol and ether to give 4-(3-acetoxy-4-methylanilino)-7-benzyloxy-6-methoxyquinazoline hydrochloride (2.69 g, 89%).

Workup

  1. temperatureheated
  2. temperatureat reflux for 1 hour
  3. filtrationThe precipitate was filtered off
  4. washwashed with isopropanol and ether

Sources & evidence

ORD record
ord-a0f01ed59988468b87dd2fbd0e69b4a0
Source dataset
uspto-grants-2002_03
Patent number
US06362336B1

Reaction notes

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