Hydrochloric Acid → Quinazoline

HRID 1456840Notes

Reaction equation

HRID 1456840 reaction equation
[N+:1]([C:4]1[CH:11]=[C:10](OC)[CH:9]=[C:8](Cl)[C:5]=1[CH:6]=O)([O-])=O.C(O)C.Cl.Cl.[NH2:20][C:21](N)=N>C1C=CC=CC=1.[Fe]>[N:1]1[C:4]2[C:5](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[N:20][CH:21]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 5742Guanidine HydrochlorideHCID 221074612-Chloro-4-methoxy-6-nitrobenzaldehyde

Product 1

HCID 9210Quinazoline

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 241BenzeneSolvent

Procedure

The nitro group of 2-nitro-4-methoxy-6-chlorobenzaldehyde (1 equivalent) is reduced to the amine by refluxing in benzene or ethanol with iron powder (the powder having been pretreated with concentrated hydrochloric acid). This amine is then treated with guanidine hydrochloride as described above (step k) to yield the quinazoline (COMPOUND XXIII) which is purified by column chromatography and/or crystallization. Benzoylation of this product is performed as described above (step d), to yield COMPOUND XXII.

Sources & evidence

ORD record
ord-9c020874a93547de96d5d5068091a6a9
Source dataset
uspto-grants-1998_12
Patent number
US05844110

Reaction notes

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