4-Hydroxybenzaldehyde → 2-(4-hydroxyphenyl)-5,7-dimethoxyquinazolin-4(3H)-one

HRID 555468Notes

Reaction equation

HRID 555468 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[C:7]([O:13][CH3:14])[C:3]=1[C:4]([NH2:6])=[O:5].[OH:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=1.C([O-])([O-])=O.[K+].[K+].II>CN(C=O)C>[OH:15][C:16]1[CH:23]=[CH:22][C:19]([C:20]2[NH:6][C:4](=[O:5])[C:3]3[C:2](=[CH:10][C:9]([O:11][CH3:12])=[CH:8][C:7]=3[O:13][CH3:14])[N:1]=2)=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 807IodineHCID 11430Potassium CarbonateHCID 203490162-Amino-4,6-dimethoxybenzamide

Product 1

HCID 1360380002-(4-hydroxyphenyl)-5,7-dimethoxyquinazolin-4(3H)-oneYield 12%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

2-Amino-4,6-dimethoxy-benzamide (328 mg, 1.67 mmol), 4-hydroxybenzaldehyde (204 mg, 1.67 mmol), K2CO3 (231 mg, 1.67 mmol) and I2 (508 mg, 2.0 mmol) were mixed in DMF (10 mL) and the reaction mixture was heated at 70° C. for 5 h. It was cooled to room temperature and poured into crushed ice. The solid was collected and purified by column chromatography (silica gel 230-400 mesh; 5% methanol in CH2Cl2 as eluent) to give 2-(4-hydroxyphenyl)-5,7-dimethoxyquinazolin-4(3H)-one (60 mg, 12%), as an off-white solid. Selected data: MS (m/z): 299.05; MP 303-305° C.

Workup

  1. temperatureIt was cooled to room temperature
  2. additionpoured
  3. custominto crushed ice
  4. customThe solid was collected
  5. custompurified by column chromatography (silica gel 230-400 mesh; 5% methanol in CH2Cl2 as eluent)

Sources & evidence

ORD record
ord-490c847ebf4a4be580769e265af0cb62
Source dataset
uspto-grants-2011_11
Patent number
US08053440B2

Reaction notes

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