HCID 58481118, compound → HCID 67365667, compound

HRID 1625707Notes

Reaction equation

HRID 1625707 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH:11]([NH2:15])[C:12]([OH:14])=[O:13])=[CH:6][C:5]=1[N+:16]([O-])=O)(=[O:3])[CH3:2]>CO.[Pd]>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH:11]([NH2:15])[C:12]([OH:14])=[O:13])=[CH:6][C:5]=1[NH2:16])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 58481118HCID 58481118, compound

Product 1

HCID 67365667HCID 67365667, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3-(4-acetyl-3-nitrophenyl)-2-aminopropanoic acid was reduced by 5% Pd on carbon in MeOH under 1 atm H2. Filtration followed by concentration under reduced pressure afforded 3-(4-Acetyl-3-aminophenyl)-2-aminopropanoic acid (X3179-96). MS (ESI+): m/z 223.22 (MH+). 1H NMR (400 MHz, MeOD): δ 7.78 (d, J=8.4 Hz, 1H), 6.66 (s, 1H), 6.54 (d, J=8.4 Hz, 1H), 4.25 (dd, J′=8.4 Hz, J″=5.2 Hz, 1H), 3.23 (dd, J′=14.4 Hz, J″=5.2 Hz, 1H), 3.02 (dd, J′=14.4 Hz, J″=8.4 Hz, 1H), 2.54 (s, 3H); 13C NMR: δ 202.14, 171.20, 152.93, 142.51, 134.40, 118.78, 118.23, 116.91, 54.63, 37.42, 27.90.

Workup

  1. filtrationFiltration
  2. concentrationfollowed by concentration under reduced pressure

Sources & evidence

ORD record
ord-79109e5539854c72979d4cb63b40eaea
Source dataset
uspto-grants-2014_07
Patent number
US08785151B2

Reaction notes

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