Methyl 4-aminobenzoate → 6,7-Dimethoxyquinazoline

HRID 2233270Notes

Reaction equation

HRID 2233270 reaction equation
NC1C=CC(C(OC)=O)=CC=1.Cl[C:13]1[C:22]2[C:17](=[CH:18][C:19]([O:25][CH3:26])=[C:20]([O:23][CH3:24])[CH:21]=2)[N:16]=[CH:15][N:14]=1>C(O)(C)C>[CH3:24][O:23][C:20]1[CH:21]=[C:22]2[C:17](=[CH:18][C:19]=1[O:25][CH3:26])[N:16]=[CH:15][N:14]=[CH:13]2

Participants

4

Reactant 2

HCID 12082Methyl 4-aminobenzoateHCID 27693644-Chloro-6,7-dimethoxyquinazoline

Product 1

HCID 30316616,7-DimethoxyquinazolineYield 190.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of methyl 4-aminobenzoate (151 mg, 1.00 mmol) and 4-chloro-6,7-dimethoxyquinazoline (224 mg, 1.00 mmol) in isopropanol (200 ml) was heated at reflux for 3 hours before the reaction was allowed to cool to ambient temperature. The solid which had precipitated was collected by suction filtration and washed with diethyl ether (2×50 ml). Drying of this material yielded 4-(4-carbomethoxy)anilino)-6,7-dimethoxyquinazoline (363 mg, 97% yield) as a white solid:

Workup

  1. temperatureat reflux for 3 hours before the reaction
  2. customThe solid which had precipitated
  3. filtrationwas collected by suction filtration
  4. washwashed with diethyl ether (2×50 ml)
  5. customDrying of this material

Sources & evidence

ORD record
ord-cfdc806089314ec5b71728e56a7d9c81
Source dataset
uspto-grants-2010_05
Patent number
US07709479B1

Reaction notes

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