Anthranilic Acid → Quinazoline

HRID 725808Notes

Reaction equation

HRID 725808 reaction equation
C([C:4]1O[N:6]=[C:7]2[C:12]=1[CH:11]=[CH:10][CH:9]=[CH:8]2)(=O)C.[ClH:13].C(O)(=O)C1[C:16](=CC=CC=1)[NH2:17].C(Cl)([Cl:26])=O.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl>CO>[ClH:26].[Cl:13][C:7]([NH2:6])=[NH:17].[N:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:4]=[N:17][CH:16]=1

Participants

8

Reactant 5

HCID 227Anthranilic AcidHCID 313Hydrochloric AcidHCID 6371PhosgeneHCID 94429TriphosgeneHCID 59777126HCID 59777126, compound

Product 2

HCID 9210QuinazolineHCID 3084509Chloroformamidinium chloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

treating the acetylanthranil compound of step (4) with MeOH, followed by hydrochloric acid, to obtain a compound of the formula: ##STR46## (5a') treating the anthranilic acid of step (3) with phosgene or triphosgene to form a compound of the formula: ##STR47## which is further treated with methanol; (5b) reacting the product of step (5a) or (5a') with chloroformamidine hydrochloride to obtain a quinazoline compound of the formula: ##STR48## then subjecting the resulting quinazoline compound to a displacement reaction as set forth in step (6) discussed above to obtain a compound according to formula I.

Workup

  1. customto obtain a compound of the formula
  2. customto form a compound of the formula

Sources & evidence

ORD record
ord-17b21322d8424b63bb7a6142d9f02dee
Source dataset
uspto-grants-1998_01
Patent number
US05707992

Reaction notes

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