Formamide → 4-Chloro-7-fluoro-6-nitroquinazoline

HRID 1255969Notes

Reaction equation

HRID 1255969 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9](F)[CH:8]=[CH:7][C:3]=1C(O)=O.[CH:12]([NH2:14])=O.[F:15][C:16]1C=C2C(C(O)=NC=N2)=CC=1.[N+:27]([O-:30])(O)=[O:28].S(=O)(=O)(O)O.[F:36][C:37]1[CH:46]=[C:45]2[C:40]([C:41](O)=[N:42][CH:43]=[N:44]2)=[CH:39][C:38]=1[N+:48]([O-:50])=[O:49].S(Cl)([Cl:53])=O>CN(C=O)C>[Cl:53][C:41]1[C:40]2[C:45](=[CH:46][C:37]([F:36])=[C:38]([N+:48]([O-:50])=[O:49])[CH:39]=2)[N:44]=[CH:43][N:42]=1.[Cl:53][C:2]1[C:3]2[C:12](=[CH:10][CH:9]=[C:8]([N+:27]([O-:30])=[O:28])[CH:7]=2)[N:14]=[C:16]([F:15])[N:1]=1

Participants

10

Reactant 7

HCID 713FormamideHCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 24386Thionyl ChlorideHCID 27249674-Fluoroanthranilic acidHCID 178518022HCID 178518022, compound2×HCID 178526403HCID 178526403, compound2×

Product 2

HCID 106093584-Chloro-7-fluoro-6-nitroquinazolineHCID 87756995HCID 87756995, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Chloro-7-fluor-6-nitroquinazoline was prepared as described in Mishani et al. (2005). In brief, 2-amino-4-fluorobezoic acid was reacted with formamide, at 160° C. for 3 hours. The resulting 7-fluoro-4-hydroxyquinazoline (Compound 22) was then reacted with a mixture of nitric acid and sulfuric acid, at 100° C., for 2 hours, to thereby obtain 7-fluoro-4-hydroxy-6-nitroquinazoline (Compound 23), which was thereafter reacted with thionyl chloride in DMF (reflux, 7 hours), to obtain 4-chloro-fluoro-6-nitroquinazoline (Compound 24, see, FIG. 3).

Sources & evidence

ORD record
ord-6f2573759f40405990c81c5ffd7ef37e
Source dataset
uspto-grants-2013_06
Patent number
US08461166B2

Reaction notes

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