HCID 21249784, compound → HCID 21249769, compound

HRID 1531624Notes

Reaction equation

HRID 1531624 reaction equation
[C:1]([O:6][CH2:7][CH2:8][O:9][C:10](=[O:23])[C:11]1[CH:16]=[C:15]([N+:17]([O-])=O)[CH:14]=[C:13]([N+:20]([O-])=O)[CH:12]=1)(=[O:5])[CH:2]([CH3:4])[CH3:3].[H][H]>[C].[Pd].C(O)C>[C:1]([O:6][CH2:7][CH2:8][O:9][C:10](=[O:23])[C:11]1[CH:12]=[C:13]([NH2:20])[CH:14]=[C:15]([NH2:17])[CH:16]=1)(=[O:5])[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 21249784HCID 21249784, compound2×HCID 178418361HCID 178418361, compound4×

Product 1

HCID 21249769HCID 21249769, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Conditions

Temperature
7 °C

Procedure

9 g of 5% palladium carbon, 90 g (0.27 mol) of 2-(3,5-dinitrobenzoyloxy)ethyl isobutyrate (compound 3) and 900 ml of ethanol were placed in a 5-l autoclave equipped with a thermocouple thermometer and a mixing blade, and the autoclave was sealed. The atmosphere inside the autoclave was replaced by hydrogen and the hydrogen pressure was increased to 5 kg/cm2. The autoclave contents were stirred at room temperature (7° C.). 10 minutes later, the autoclave inside temperature rose to 34° C. and the autoclave inside pressure dropped to 1 kg/cm2. Then, hydrogen was introduced to raise the pressure to 5 kg/cm2, and stirring was continued. Ten minutes later, the temperature became 50° C. and the pressure dropped to 1 kg/cm2. Hydrogen was again introduced to raise the pressure to 5 kg/cm2, and stirring was continued. Since the temperature began to drop and the pressure became constant (4 kg/cm2), stirring was continued for 100 minutes (the temperature dropped to 18° C.). The atmosphere inside the autoclave was replaced by nitrogen, and the autoclave contents were taken out and filtered to remove palladium carbon. The filtrate was concentrated by the use of an evaporator, whereby a solid was separated. The solid was recrystallized from 200 ml of toluene to obtain 2-(3,5-diaminobenzoyloxy)ethyl isobutyrate (compound 4). Yield: 60 g (83%) Melting point: 81-83° C.

Workup

  1. customequipped with a thermocouple thermometer
  2. customa mixing blade, and the autoclave was sealed
  3. custom10 minutes
  4. customrose to 34° C.
  5. additionthe autoclave inside pressure dropped to 1 kg/cm2
  6. temperatureto raise the pressure to 5 kg/cm2
  7. stirringstirring
  8. customTen minutes
  9. custombecame 50° C.
  10. additionthe pressure dropped to 1 kg/cm2
  11. temperatureto raise the pressure to 5 kg/cm2
  12. stirringstirring
  13. stirringstirring
  14. addition(the temperature dropped to 18° C.)
  15. filtrationfiltered
  16. customto remove palladium carbon
  17. concentrationThe filtrate was concentrated by the use of an evaporator, whereby a solid
  18. customwas separated
  19. customThe solid was recrystallized from 200 ml of toluene

Sources & evidence

ORD record
ord-065e3623127d45f8bf75237ae03ce15a
Source dataset
uspto-grants-2001_03
Patent number
US06200831B1

Reaction notes

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