Anthranilamide → HCID 178525385, compound

HRID 1402942Notes

Reaction equation

HRID 1402942 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:14][C:13](=[O:15])[O:12][C:10](=O)[CH2:9]2)=[CH:4][CH:3]=1.[C:16]([NH2:25])(=[O:24])[C:17]1[C:18](=[CH:20][CH:21]=[CH:22][CH:23]=1)[NH2:19]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH2:9][C:10]2[N:25]=[C:16]([OH:24])[C:17]3[C:18](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:19]=2)[CH2:14][C:13]([OH:12])=[O:15])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6942AnthranilamideHCID 1046394-(4-Chlorophenyl)dihydro-2H-pyran-2,6(3H)-dione

Product 1

HCID 178525385HCID 178525385, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The solution of 3-(4-chlorophenyl)glutaric anhydride (449 mg) and anthranilamide (272 mg) in toluene (8 ml) was heated to reflux for 4 h. After removal of the solvent the residue was dried in vacuo. The off-white solid was dissolved in 2M sodium hydroxide (3 ml) and stirred under reflux for 2 h. After cooling to room temperature acetic acid (0.5 ml) was added with stirring. The precipitate formed was isolated by suction filtration, washed, and dried in vacuo to give 3-(4-chlorophenyl)-4-(4-hydroxy-2-quinazolinyl)butanoic acid (0.57 g) as colourless solid.

Workup

  1. temperatureto reflux for 4 h
  2. customAfter removal of the solvent the residue
  3. customwas dried in vacuo
  4. dissolutionThe off-white solid was dissolved in 2M sodium hydroxide (3 ml)
  5. temperatureunder reflux for 2 h
  6. additionwas added
  7. stirringwith stirring
  8. customThe precipitate formed
  9. customwas isolated by suction filtration
  10. washwashed
  11. customdried in vacuo

Sources & evidence

ORD record
ord-a0f93d462c4f4e0989a2251431b3d981
Source dataset
uspto-grants-2014_12
Patent number
US08912186B2

Reaction notes

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