Hydrochloric Acid → 3-(1-Aminoethyl)benzoic acid hydrochloride

HRID 467502Notes

Reaction equation

HRID 467502 reaction equation
O[N:2]=[C:3]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9])[CH3:4].[ClH:14]>[Pd].C(O)C>[ClH:14].[NH2:2][CH:3]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9])[CH3:4]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 766866363-(1-(Hydroxyimino)ethyl)benzoic acid

Product 1

HCID 534076803-(1-Aminoethyl)benzoic acid hydrochlorideYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3-(1-(Hydroxyimino)ethyl)benzoic acid (2.28 g, 12.73 mmol) and palladium on carbon (10 wt. %, 1.355 g, 12.73 mmol) in ethanol (170 mL) and 12M aqueous HCl (2.1 mL, 24.2 mmol) were stirred under an atmosphere of H2 at 40 psi for 6 hours. The reaction mixture was purged with nitrogen for 30 minutes then filtered through a pad of Celite washing with methanol. The filtrate was concentrated in vacuo and the residue triturated from Et2O to give the sub-title compound as a white (2.4 g, 94% Yield). 1H NMR (400 MHz, CD3OD) δ 1.66 (d, 3H), 4.55 (q, 1H), 7.58 (t, 1H), 7.70 (d, 1H), 8.07 (d, 1H) and 8.16 (s, 1H); MS (ES+) 166.5.

Workup

  1. customThe reaction mixture was purged with nitrogen for 30 minutes
  2. filtrationthen filtered through a pad of Celite
  3. washwashing with methanol
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue triturated from Et2O

Sources & evidence

ORD record
ord-28f9f8cad73e4e5e914d48248634e69b
Source dataset
uspto-grants-2014_01
Patent number
US08623869B2

Reaction notes

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