Hydrochloric Acid → 4-(N-Methylphenylamino)-2-(2-methyl-4-fluorophenylamino)-6-methoxyquinazoline

HRID 973579Notes

Reaction equation

HRID 973579 reaction equation
Cl[C:2]1[N:11]=[C:10]([N:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:20][CH3:21])[CH:8]=2)[N:3]=1.[F:22][C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[C:25]([CH3:30])[CH:24]=1.Cl>C(O)C>[CH3:13][N:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:20][CH3:21])[CH:8]=2)[N:3]=[C:2]([NH:27][C:26]2[CH:28]=[CH:29][C:23]([F:22])=[CH:24][C:25]=2[CH3:30])[N:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 679824-Fluoro-2-methylanilineHCID 100861382-Chloro-4-(N-methylphenylamino)-6-methoxyquinazoline

Product 1

HCID 102496764-(N-Methylphenylamino)-2-(2-methyl-4-fluorophenylamino)-6-methoxyquinazolineYield 54.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Chloro-4-(N-methylphenylamino)-6-methoxyquinazoline (5.4 g, 0.02M) and 4-fluoro-2-methylaniline (4.96 g, 0.04M) were dissolved in ethanol (50 ml) and heated at 140° for 5 hours in a Berghof pressure reactor. The mixture was cooled and ethereal/HCl added. The precipitated solid was filtered off and recrystallised (isopropanol/ether followed by isopropanol) to yield the title compound (3.8 g) m.p. 248°-250°.

Workup

  1. temperatureheated at 140° for 5 hours in a Berghof pressure reactor
  2. temperatureThe mixture was cooled
  3. filtrationThe precipitated solid was filtered off
  4. customrecrystallised (isopropanol/ether followed by isopropanol)

Sources & evidence

ORD record
ord-d078d3e282ec4b898f264c21c6715b45
Source dataset
uspto-grants-1991_11
Patent number
US05064833

Reaction notes

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