N-(o-Nitrobenzyl)ethyl glycine → N-(o-Aminobenzyl)ethyl glycine

HRID 1579987Notes

Reaction equation

HRID 1579987 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][CH:15]=[CH:14][C:5]=1[CH2:6][CH2:7][CH2:8][NH:9][CH2:10][C:11]([OH:13])=[O:12])([O-])=O.[H][H]>[Pd].C(O)C>[NH2:1][C:4]1[CH:17]=[CH:16][CH:15]=[CH:14][C:5]=1[CH2:6][CH2:7][CH2:8][NH:9][CH2:10][C:11]([OH:13])=[O:12]

Participants

5

Reactant 2

HCID 57139570N-(o-Nitrobenzyl)ethyl glycineHCID 178418361HCID 178418361, compound

Product 1

HCID 57043355N-(o-Aminobenzyl)ethyl glycineYield 77%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 13.0 g. (5.46 × 10-2 moles) of N-(o-nitrobenzyl)ethyl glycine in 200 ml. of absolute ethyl alcohol was added slowly 0.76 g. (5% by weight) of 10% Pd/C catalyst and the mixture placed on a Paar hydrogenator. The mixture was shaken until theoretical hydrogen (16.4 × 10-2 moles) had been absorbed, removed from the Paar and the mixture filtered under suction. The catalyst was washed with ethyl alcohol and the solvent removed in vacuo affording a yellow oil. Purification of the oil was effected by distillation yielding 8.8 g. (77% yield) of a colorless oil; b.p. 124°-126°C. (0.03 mm).

Workup

  1. customhad been absorbed
  2. customremoved from the Paar
  3. filtrationthe mixture filtered under suction
  4. washThe catalyst was washed with ethyl alcohol
  5. customthe solvent removed in vacuo
  6. customaffording a yellow oil
  7. customPurification of the oil
  8. distillationwas effected by distillation
  9. customyielding 8.8 g

Sources & evidence

ORD record
ord-fe975d707ff3407482e67275db8a1cc6
Source dataset
uspto-grants-1976_01
Patent number
US03932407

Reaction notes

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