Hydrochloric Acid → Ethyl [3-(aminomethyl)phenyl]acetate--hydrogen chloride (1/1)

HRID 2067156Notes

Reaction equation

HRID 2067156 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH2:9][C:10]([OH:12])=[O:11])[CH:6]=[CH:7][CH:8]=1)#[N:2].[ClH:13].[CH2:14](O)[CH3:15]>[Pd]>[ClH:13].[NH2:2][CH2:1][C:3]1[CH:4]=[C:5]([CH2:9][C:10]([O:12][CH2:14][CH3:15])=[O:11])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 15193972-(3-Cyanophenyl)acetic acid

Product 1

HCID 69544396Ethyl [3-(aminomethyl)phenyl]acetate--hydrogen chloride (1/1)

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of (3-cyanophenyl)acetic acid (3 g, 18.6 mmol), 10% palladium on charcoal (300 mgs) and conc. hydrochloric acid (3 eqs, 4.6 mls, 55.8 mmol) in ethanol (100 mls) was subject to an atmosphere of hydrogenation overnight. The resulting mixture was filtered through hyflo and the catalyst washed thoroughly with ethanol. The solvent was then evaporated in vacuo to give a crunchy white solid. This was triturated with ether, filtered off and dried to afford a white solid (2.76 g). 1H-NMR (400 MHz, d4-MeOH) δ 1.24 (3H,t, J 8.0), 3.69 (2H,s), 4.11 (2H,s), 4.15 (2H,q, J 13.2 6.0), 7.17-7.20 (1H, m), 7.34-7.44 (4H, m).

Workup

  1. customwas subject to an atmosphere of hydrogenation overnight
  2. filtrationThe resulting mixture was filtered through hyflo
  3. washthe catalyst washed thoroughly with ethanol
  4. customThe solvent was then evaporated in vacuo
  5. customto give a crunchy white solid
  6. customThis was triturated with ether
  7. filtrationfiltered off
  8. customdried

Sources & evidence

ORD record
ord-d25317820ada4ca9971cf1ed2e1bdf73
Source dataset
uspto-grants-2012_10
Patent number
US08293798B2

Reaction notes

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