2,4-Dinitrophenylacetic acid → 2-(2,4-diaminophenyl)acetic acid

HRID 1844102Notes

Reaction equation

HRID 1844102 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[CH:6][C:5]=1[CH2:13][C:14]([OH:16])=[O:15])([O-])=O.[H][H]>CO.[Pd]>[NH2:1][C:4]1[CH:9]=[C:8]([NH2:10])[CH:7]=[CH:6][C:5]=1[CH2:13][C:14]([OH:16])=[O:15]

Participants

5

Reactant 2

HCID 2215132,4-Dinitrophenylacetic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 2262622-(2,4-diaminophenyl)acetic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To 2,4-dinitrophenylacetic acid (1.2 gm) in methanol (60 mL), added Pd/C (80 mg, 10 wt %). H2 gas environment was maintained with pressure using hydrogen gas balloon and solution stirred for 6 hours at RT. The catalyst was removed by filtration, over celite. The filtrate was concentrated in vacuo to give 2,4-diaminophenylacetic acid without further purification, immediately refluxed with 16 ml of 1N HCl for 6 hrs. Reaction was monitored with TLC. The solution was neutralized with 1% sodium hydroxide, extracted with three portions of ethyl acetate. The organic layers were combined, dried over anhydrous sodium sulfate or magnesium sulfate, evaporated in vacuo to get the title compound D4: YD: 67.85%: mp: 193-195° C.; Rf: 0.358 (EA:Hx: 7.0:3.0). 1H NMR (DMSO-d6) 200 MHz, δ: 3.227 (s, 2H), 5.004 (s, 2H) —NH2, 6.094 (dd, J=2.2 & 6.2 Hz, 1H), 6.098 (d, J=2.0 Hz, 1H), 6.786 (d, J=8.4 Hz, 1H), 10.088 (s, 1H). MS (ESI): m/z 146.8 [M−H]−.

Workup

  1. temperatureH2 gas environment was maintained with pressure
  2. customThe catalyst was removed by filtration, over celite
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-ca20af4b0c504da9935d3998624666f0
Source dataset
uspto-grants-2015_02
Patent number
US08946282B2

Reaction notes

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