Ethanol → Ethyl 4,5-diamino-2-ethoxy-benzoate

HRID 578057Notes

Reaction equation

HRID 578057 reaction equation
C([NH:8][C:9]1[C:19]([N+:20]([O-])=O)=[CH:18][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:11]([O:23][CH2:24][CH3:25])[CH:10]=1)C1C=CC=CC=1.C(O)C>[Pd].C1COCC1>[NH2:8][C:9]1[C:19]([NH2:20])=[CH:18][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:11]([O:23][CH2:24][CH3:25])[CH:10]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 67233615Ethyl 4-benzylamino-2-ethoxy-5-nitro-benzoate

Product 1

HCID 67229822Ethyl 4,5-diamino-2-ethoxy-benzoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Palladium on charcoal (3.50 g 10%) was added to the product obtained at (655c) (16.7 g, 46.1 mmol) in 200 mL THF with 200 mL ethanol and the mixture was hydrogenated using a Parr apparatur at 60 psi H2 pressure and 50° C. for 3 h. The mixture was filtered, washed with ethanol and the filtrate concentrated i. vac. The residue was triturated with dichloromethane and evaporated to dryness. The product was reacted without further purification.

Workup

  1. customat 60 psi H2 pressure and 50° C.
  2. customfor 3 h
  3. filtrationThe mixture was filtered
  4. washwashed with ethanol
  5. concentrationthe filtrate concentrated i
  6. customThe residue was triturated with dichloromethane
  7. customevaporated to dryness
  8. customThe product was reacted without further purification

Sources & evidence

ORD record
ord-f2236cc87619431e88883eb50219acde
Source dataset
uspto-grants-2015_05
Patent number
US09040565B2

Reaction notes

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