Sodium → HCID 54308116, compound

HRID 1729624Notes

Reaction equation

HRID 1729624 reaction equation
[C:1]([CH2:5][CH2:6][C:7]([NH:9][C:10]1[C:11](=[CH:15][CH:16]=[C:17]([Cl:19])[CH:18]=1)[C:12]([O-:14])=O)=[O:8])([O:3][CH3:4])=[O:2].[Na]>C1(C)C=CC=CC=1>[CH3:4][O:3][C:1]([CH:5]1[C:12](=[O:14])[C:11]2[CH:15]=[CH:16][C:17]([Cl:19])=[CH:18][C:10]=2[NH:9][C:7](=[O:8])[CH2:6]1)=[O:2]

Participants

4

Reactant 2

HCID 5360545SodiumHCID 21500132HCID 21500132, compound

Product 1

HCID 54308116HCID 54308116, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

The solution of 264 g of N-(3-carbomethoxypropionyl)-4-chloroanthranilate in 1.8 lt of warm toluene is added dropwise to the hot suspension of 42.6 g of sodium in 900 ml of toluene while stirring and the mixture is refluxed for 5 hours. It is cooled, filtered, the residue taken up in 6 lt of water, the pH of the solution adjusted to 3 with 3N hydrochloric acid, the precipitate formed filtered off, washed with water and recrystallized from acetic acid, to yield the 8-chloro-2,3,4,5-tetrahydro-1-benzazepine-2,5-dione-4-carboxylic acid methyl ester melting at 270°-272°.

Workup

  1. temperaturethe mixture is refluxed for 5 hours
  2. temperatureIt is cooled
  3. filtrationfiltered
  4. customthe precipitate formed
  5. filtrationfiltered off
  6. washwashed with water
  7. customrecrystallized from acetic acid

Sources & evidence

ORD record
ord-87b76332529647968f4f2db1f9056589
Source dataset
uspto-grants-1976_11
Patent number
US03989689

Reaction notes

Loading…