Maleic Anhydride → HCID 53786874, compound

HRID 394765Notes

Reaction equation

HRID 394765 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]=[C:5]2[NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Br:19])[CH:14]=1.[C:20]1(=[O:26])[O:25][C:23](=[O:24])[CH:22]=[CH:21]1>CN(C=O)C.O>[Br:19][C:15]1[CH:14]=[C:13]([NH:12][C:5]2[C:4]3[C:9](=[CH:10][CH:11]=[C:2]([NH:1][C:20]([CH:21]=[CH:22][C:23]([OH:25])=[O:24])=[O:26])[CH:3]=3)[N:8]=[CH:7][N:6]=2)[CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 7923Maleic AnhydrideHCID 5328042N4-(3-Bromophenyl)quinazoline-4,6-diamine

Product 1

HCID 53786874HCID 53786874, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 6-amino-4-[(3-bromophenyl)amino]-quinazoline (0.78 g, 2.5 mmol) in 8 mL of DMF was added maleic anhydride (0.266 g, 2.7 mmol), and the mixture was heated with stirring in a 70° C. oil bath for 2.5 hours. The resulting suspension was cooled to room temperature and then diluted with water. The solid was collected, washed sequentially with a mixture of toluene/DMF (1:1), water, and IPA. The solid was dried in vacuo at 60° C. for 16 hours to afford 3-[4-(3-bromo-phenylamino)-quinazolin-6-ylcarbamoyl]-acrylic acid (Z) (0.87 g, 86%) as a pale yellow powder, mp 224-225° C. (decomposition with gas evolution).

Workup

  1. temperaturethe mixture was heated
  2. temperatureThe resulting suspension was cooled to room temperature
  3. customThe solid was collected
  4. washwashed sequentially with a mixture of toluene/DMF (1:1), water, and IPA
  5. customThe solid was dried in vacuo at 60° C. for 16 hours

Sources & evidence

ORD record
ord-40baa3e784934ea3a237670fa73e639c
Source dataset
uspto-grants-2003_08
Patent number
US06602863B1

Reaction notes

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