HCID 10609959, compound → HCID 10607076, compound

HRID 1378740Notes

Reaction equation

HRID 1378740 reaction equation
C([O:3][C:4](=O)[CH2:5][NH:6][C:7]1[C:12]([CH3:13])=[CH:11][CH:10]=[CH:9][C:8]=1[N+:14]([O-])=O)C>[Pd].C(O)C>[CH3:13][C:12]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:7]=1[NH:6][CH2:5][C:4](=[O:3])[NH:14]2

Participants

4

Reactant 1

HCID 10609959HCID 10609959, compound

Product 1

HCID 10607076HCID 10607076, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of N-(6-methyl-2-nitrophenyl)glycine ethyl ester (XV, EXAMPLE 17, 675 mg), ethanol (60.0 ml) and palladium on carbon (10%, 150 mg) is hydrogenated (48 psi) at 20°-25° for 3.5 hr. The mixture is filtered, the residue washed with ethanol, and the combined filtrates are concentrated to give the title compound, mp 168°-171°; IR (mineral oil) 3382, 2955, 2925, 1671, 1490, 1444, 1393, 1295 and 770 cm-1 ; NMR (CDCl3) 8.68, 6.79, 6.6-6.75, 4.04, 3.76 and 2.17 δ; MS (m/z) 162 and 133.

Workup

  1. customat 20°-25°
  2. customfor 3.5 hr
  3. filtrationThe mixture is filtered
  4. washthe residue washed with ethanol
  5. concentrationthe combined filtrates are concentrated

Sources & evidence

ORD record
ord-bb1c84bb76834ef6814dec2665869d95
Source dataset
uspto-grants-1997_09
Patent number
US05668282

Reaction notes

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