Hydrochloric Acid → HCID 54334488, compound

HRID 849273Notes

Reaction equation

HRID 849273 reaction equation
[NH2:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1.[CH3:12][C:13]1=[C:14]([CH3:20])[C:15]([O:17][C:18]1=O)=[O:16].[ClH:21]>[OH-].[Na+].CC(N(C)C)=O>[CH3:12][C:13]1[C:18](=[O:17])[N:1]([CH2:2][C:3]2[CH:4]=[CH:5][C:6]([C:7]([Cl:21])=[O:9])=[CH:10][CH:11]=2)[C:15](=[O:16])[C:14]=1[CH3:20]

Participants

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 13010Dimethylmaleic anhydrideHCID 655264-(Aminomethyl)Benzoic Acid

Product 1

HCID 54334488HCID 54334488, compound

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
90 °C

Procedure

100 g (0.66 mol) of 4-(aminomethyl)-benzoic acid are dissolved in sodium hydroxide solution (26.4 g of NaOH in 300 ml of water). There is added dropwise to that solution, with stirring, a solution of 83.3 g of dimethylmaleic acid anhydride in 500 ml of dimethylacetamide. The reaction solution is then heated at 90° C. and, after 1.5 hours, 330 ml of aqueous hydrochloric acid (2N) are added. After the addition of hydrochloric acid the solution is cooled to room temperature and the stirrer is switched off. The crystalline product that has precipitated is filtered off, washed with water and dried in vacuo at 60° C. Yield: 155 g (90%). Melting point: 182-183° C. 120 g of that intermediate are suspended in 1000 ml of dry toluene. At 70° C., 50 ml of thionyl chloride are added dropwise. As soon as the evolution of gas has ceased (approx. 2 hours), the temperature is increased to 80° C. for 2 hours. After cooling, the solution is concentrated. The solid residue is recrystallised in toluene and then dried at 60° C. Yield: 155 g (80%). Melting point: 98-99° C. 1H-NMR (CDCl3): 1.98 (s, CH3), 4.72 (s, CH2), 7.45 (d, phenyl), 8.06 (d, phenyl).

Workup

  1. additionThere is added dropwise to that solution
  2. temperatureis cooled to room temperature
  3. customThe crystalline product that has precipitated
  4. filtrationis filtered off
  5. washwashed with water
  6. customdried in vacuo at 60° C
  7. additionAt 70° C., 50 ml of thionyl chloride are added dropwise
  8. custom(approx. 2 hours)
  9. temperaturethe temperature is increased to 80° C. for 2 hours
  10. temperatureAfter cooling
  11. concentrationthe solution is concentrated
  12. customThe solid residue is recrystallised in toluene
  13. customdried at 60° C

Sources & evidence

ORD record
ord-64ad319ca7ae4c64a11fffa32ad7821a
Source dataset
uspto-grants-2000_01
Patent number
US06011149

Reaction notes

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