2-Ethoxy-3-(4-nitrophenyl)prop-2-enoic acid → HCID 11424340, compound

HRID 2370478Notes

Reaction equation

HRID 2370478 reaction equation
[CH2:1]([O:3][C:4](=[CH:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=1)[C:5]([OH:7])=[O:6])[CH3:2]>CO.[Pd]>[CH2:1]([O:3][CH:4]([CH2:8][C:9]1[CH:10]=[CH:11][C:12]([NH2:15])=[CH:13][CH:14]=1)[C:5]([OH:7])=[O:6])[CH3:2]

Participants

4

Reactant 1

HCID 669056312-Ethoxy-3-(4-nitrophenyl)prop-2-enoic acid

Product 1

HCID 11424340HCID 11424340, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-Ethoxy-3-(4-nitrophenyl)acrylic acid (18.4 g wet, approx. 77.5 mmol) was dissolved in MeOH (1.1 L) and 10% Pd on C (wet basis) (1.84 g) was added. The mixture was hydrogenated at 12 psi for 10 mins, followed by repeated refill to 20-28 psi every 10-m 20 mins for 5 hr then 46 psi for 18 hr. The mixture was filtered through GF/F paper and the residue was slurried in IMS (100 ml), filtered, washed with heptane (100 ml), and suction dried on the filter. Thus (±)-2-ethoxy 3-(4′-Aminophenyl)-propionic acid was obtained as an off-white solid (11.2 g, 69%).

Workup

  1. customfor 5 hr
  2. wait46 psi for 18 hr
  3. filtrationThe mixture was filtered through GF/F paper
  4. filtrationfiltered
  5. washwashed with heptane (100 ml), and suction
  6. customdried on the filter

Sources & evidence

ORD record
ord-d7daae631ef5409094772885027bc928
Source dataset
uspto-grants-2014_04
Patent number
US08710100B2

Reaction notes

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