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

HRID 572201Notes

Reaction equation

HRID 572201 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]>[Pd].CO>[NH2:12][C@H:10]([C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[NH2:1])[CH3:11]

Participants

5

Reactant 2

HCID 11292459HCID 11292459, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 40637894(S)-3-(1-aminoethyl)anilineYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (1S)-1-(3-nitrophenyl)ethanamine (13.1 g, 79.4 mmol) and 10% palladium on carbon (0.75 g) in methanol (250 mL) was stirred vigorously under an atmoshphere of hydrogen for 19 hours. After this time the mixture was filtered through a pad of Celite and the pad was washed with methanol (800 mL). The combined filtrates were concentrated under reduced pressure to give 3-[(1S)-1-aminoethyl]aniline as a brown solid (10.8 g, 100%).

Workup

  1. filtrationAfter this time the mixture was filtered through a pad of Celite
  2. washthe pad was washed with methanol (800 mL)
  3. concentrationThe combined filtrates were concentrated under reduced pressure

Sources & evidence

ORD record
ord-354355b5fa754155ae29db83bd5a85b9
Source dataset
uspto-grants-2015_05
Patent number
US09029386B2

Reaction notes

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