HCID 18536460, compound → HCID 18536458, compound

HRID 412543Notes

Reaction equation

HRID 412543 reaction equation
[C:1]([O:5][C:6](=[O:20])[CH2:7][NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][C:10]=1[N+:17]([O-])=O)([CH3:4])([CH3:3])[CH3:2]>O1CCCC1.[C].[Pd]>[C:1]([O:5][C:6](=[O:20])[CH2:7][NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][C:10]=1[NH2:17])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 18536460HCID 18536460, compound

Product 1

HCID 18536458HCID 18536458, compoundYield 53.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalyst2×HCID 8028TetrahydrofuranSolvent

Procedure

N-(4-Cyano-2-nitrophenyl)glycine tert-butyl ester (17.337 g) was hydrogenated using 7.5% palladium carbon (1.73 g) in tetrahydrofuran (173 ml) at atmospheric pressure for 2 hours and by adding 7.5% palladium carbon (3.84 g) for one more hour. After completion of the reaction, the reaction mixture was filtered through celite and the solvent was evaporated. The obtained residue was washed with diisopropyl ether, collected by filtration and dried under reduced pressure to give the title compound (8.324 g).

Workup

  1. customfor 2 hours
  2. customAfter completion of the reaction
  3. filtrationthe reaction mixture was filtered through celite
  4. customthe solvent was evaporated
  5. washThe obtained residue was washed with diisopropyl ether
  6. filtrationcollected by filtration
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-9297ab7ce3104125a563a738a288c93b
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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