3-(4-Aminophenyl)prop-2-enoic acid → 6,7-Dimethoxyquinazoline

HRID 2213857Notes

Reaction equation

HRID 2213857 reaction equation
NC1C=CC(C=CC(O)=O)=CC=1.Cl[C:14]1[C:23]2[C:18](=[CH:19][C:20]([O:26][CH3:27])=[C:21]([O:24][CH3:25])[CH:22]=2)[N:17]=[CH:16][N:15]=1>C(O)(C)C>[CH3:25][O:24][C:21]1[CH:22]=[C:23]2[C:18](=[CH:19][C:20]=1[O:26][CH3:27])[N:17]=[CH:16][N:15]=[CH:14]2

Participants

4

Reactant 2

HCID 929283-(4-Aminophenyl)prop-2-enoic acidHCID 27693644-Chloro-6,7-dimethoxyquinazoline

Product 1

HCID 30316616,7-DimethoxyquinazolineYield 184%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

As an alternative, a solution of 4-aminocinnamic acid (199 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-(2-carboxy)ethenyl)anilino)-6,7-dimethoxyquinazoline (350 mg, 90% yield) as a yellow 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-d45f803b449544ea885c43e2d471dfe2
Source dataset
uspto-grants-2006_09
Patent number
US07105669B1

Reaction notes

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