HCID 11292459, compound → (S)-3-(1-aminoethyl)aniline

HRID 2300890Notes

Reaction equation

HRID 2300890 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C@@H:10]([NH2:12])[CH3:11])[CH:7]=[CH:8][CH:9]=1)([O-])=O.[H][H]>C1COCC1.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([C@@H:10]([NH2:12])[CH3:11])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 11292459HCID 11292459, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 40637894(S)-3-(1-aminoethyl)anilineYield 38.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

(S)-1-(3-nitrophenyl)-1-aminoethane (approx. 80% pure, 75.2 mg) was dissolved in THF (2 mL) and 10% Pd/C (13.8 mg) was added. The system was fitted with a balloon of hydrogen and purged 3×, the mixture left stirring 16 h at room temperature. Filtered the solution through Celite®, washing thoroughly with methanol, and the solvent removed in vacuo. The residue was eluted on silica gel (3-6%(2M NH3 in MeOH)/CH2Cl2) to yield 23.7 mg of the title compound. 1H NMR (500 MHz, CDCl3): δ 7.13 (t, J=7.7 Hz, 1H); 6.74 (m, 1H); 6.71 (m, 1H); 6.58 (m, 1H); 4.03 (q, J=6.7 Hz, 1H); 3.68 (br s, 2H); 1.37 (d, J=6.7 Hz, 3H).

Workup

  1. custompurged 3×
  2. waitthe mixture left
  3. filtrationFiltered the solution through Celite®
  4. washwashing thoroughly with methanol
  5. customthe solvent removed in vacuo
  6. washThe residue was eluted on silica gel (3-6%(2M NH3 in MeOH)/CH2Cl2)

Sources & evidence

ORD record
ord-33fbcf79c4a74c21a57a208f6e27feef
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

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