m-Toluidine → HCID 21847809, compound

HRID 618686Notes

Reaction equation

HRID 618686 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([F:12])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[CH3:13][C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][CH:20]=1)[NH2:17]>C(O)(C)C.Cl>[ClH:1].[F:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[CH:4][N:3]=[C:2]2[NH:17][C:16]1[CH:18]=[CH:19][CH:20]=[C:14]([CH3:13])[CH:15]=1

Participants

5

Reactant 2

HCID 7934m-ToluidineHCID 130594574-Chloro-6-fluoroquinazoline

Product 1

HCID 21847809HCID 21847809, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 3776IsopropanolSolvent

Procedure

4-Chloro-6-fluoroquinazoline (1.1 g) was suspended in isopropanol (20 ml) and 3-methylaniline (0.65 ml) was added. The mixture was heated to reflux for 2 hours. The reaction mixture was allowed to cool and the precipitate was filtered off. The solid so obtained was suspended in 2N aqueous hydrochloric acid and stirred for several minutes. The mixture was filtered to give 6-fluoro-4-(3-methylanilino)quinazoline hydrochloride salt in 43% yield, m.p. 255-260° C.;

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 hours
  3. temperatureto cool
  4. filtrationthe precipitate was filtered off
  5. customThe solid so obtained
  6. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-2e41fd230b514d2da78327e6aabbe5ad
Source dataset
uspto-grants-1999_09
Patent number
US05955464

Reaction notes

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