Ethyl Acetate → 2-(4-Chlorophenyl)-4-hydroxy-6,7-dimethoxyquinazoline

HRID 2408996Notes

Reaction equation

HRID 2408996 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([NH:10][C:11]2[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[CH:16][C:12]=2[C:13]([NH2:15])=[O:14])=O)=[CH:4][CH:3]=1.[OH-].[Na+].CCOC(C)=O>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:15][C:13](=[O:14])[C:12]3[C:11](=[CH:19][C:18]([O:20][CH3:21])=[C:17]([O:22][CH3:23])[CH:16]=3)[N:10]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 229974052-(4-Chlorobenzoylamino)-4,5-dimethoxybenzamide

Product 1

HCID 1358250262-(4-Chlorophenyl)-4-hydroxy-6,7-dimethoxyquinazoline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-((4-chlorophenyl)carbonylamino)-4,5-dimethoxybenzamide (1.0 g, 2.99 mmol) in ethanol (10 mL) was added aqueous NaOH solution (15 mL) at rt for 10 min. The reaction mixture was refluxed for 10 min and allowed to rt. The mixture was poured into ice cold water and stirred for 10 min EtOAc (20 mL) was added to the solution and stirred for 5 min. The separated solid was filtered, washed with ice cold water and dried to the product as a white color solid (900 mg, 95%), mp>360° C. 1H NMR (400 MHz, DMSO-d6): δ 12.47 (1H, s), 8.19 (2H, d, J=8.6 Hz), 7.62 (2H, d, J=8.6 Hz), 7.50 (1H, s), 7.23 (1H, s), 3.94 (3H, s), 3.90 (3H, s); LC-MS (positive ion mode): m/z 317, 319 (M+H)±.

Workup

  1. temperatureThe reaction mixture was refluxed for 10 min
  2. customallowed to rt
  3. additionThe mixture was poured into ice cold water
  4. additionwas added to the solution
  5. filtrationThe separated solid was filtered
  6. washwashed with ice cold water
  7. dry with materialdried to the product as a white color solid (900 mg, 95%), mp>360° C

Sources & evidence

ORD record
ord-2bcd99d4382540b0bc8f75848a519637
Source dataset
uspto-grants-2014_08
Patent number
US08815879B2

Reaction notes

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