O-Toluidine → HCID 10086136, compound

HRID 973560Notes

Reaction equation

HRID 973560 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[C:10]([Cl:13])[N:9]=[C:8]2Cl.[NH2:15][C:16]1[C:17]([CH3:22])=[CH:18][CH:19]=[CH:20][CH:21]=1.C([O-])(=O)C.[Na+].[OH-].[Na+]>O.O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[C:10]([Cl:13])[N:9]=[C:8]2[NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH3:22]

Participants

7

Reactant 4

HCID 7242O-ToluidineHCID 14798Sodium HydroxideHCID 517045Sodium AcetateHCID 104213312,4-Dichloro-8-methoxyquinazoline

Product 1

HCID 10086136HCID 10086136, compoundYield 60.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

8-Methoxy-2,4-dichloroquinazoline (3.7 g, 0.016 mol) was stirred in a mixture of water (85 ml), tetrahydrofuran (125 ml), o-toluidine (1.7 g, 0.016 mol) and sodium acetate (2.2 g, 0.027 mol) for a total of 4 days with heating to 50° for a total of 32 hours and the addition of a total of 20 ml 0.01 mol NaOH dropwise over this period maintaining the pH at 7. The reaction mixture was evaporated in vacuo and crystallised from ethanol/water to give 8-methoxy-4-(2-methylphenylamino)-2-chloroquinazoline (2.89 g, 60%) m.p. 218°-220°.

Workup

  1. temperaturewith heating to 50° for a total of 32 hours
  2. temperaturemaintaining the pH at 7
  3. customThe reaction mixture was evaporated in vacuo
  4. customcrystallised from ethanol/water

Sources & evidence

ORD record
ord-085320eea3ba4ca18164e228ea71269f
Source dataset
uspto-grants-1991_11
Patent number
US05064833

Reaction notes

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