Hydrochloric Acid → 3-Amino-4-hydroxybenzonitrile

HRID 2218958Notes

Reaction equation

HRID 2218958 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:10]([O-])=O.[Sn].Cl.C([O-])(O)=O.[Na+]>O.C(O)C>[NH2:10][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:2]=1[OH:1])[C:6]#[N:7]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 767584-Hydroxy-3-nitrobenzonitrileHCID 516892Sodium BicarbonateHCID 5352426Tin atom

Product 1

HCID 2712583-Amino-4-hydroxybenzonitrile

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a mixture of 5 g (30.5 mmol) of 4-hydroxy-3-nitrobenzonitrile, 18.1 g of powder tin metal (152.5 mmol, 325 mesh), and 45 mL of ethanol was added with stirring a solution of 10 mL of concentrated HCl in 30 mL of H2O. The suspension was heated at reflux for 45 min and the resulting hot solution was poured into 100 mL of H2O. Saturated aqueous NaHCO3 solution was slowly added to bring the pH to ca. 7. The suspension was filtered, and the residue was washed with MeOH giving the title compound (3.15 g, 77%) as a white powder. Rf (CH2Cl2/MeOH 9:1) 0.47; 1H NMR (CD3OD) δ 6.96 (d, 1H, J=1.3 Hz, H-2), 6.92 (d, 1H, J=8.1 Hz, H-6), 6.75 (d, 1H, J=8.1 Hz, H-5); 13C NMR (CD3OD) δ 151.1 (C-4), 138.6 (C-3), 124.7 (C-6), 121.6 (CN), 119.1 (C-2), 115.9 (C-5), 103.6 (C-1).

Workup

  1. additionwas added
  2. temperatureThe suspension was heated
  3. temperatureat reflux for 45 min
  4. filtrationThe suspension was filtered
  5. washthe residue was washed with MeOH giving the title compound (3.15 g, 77%) as a white powder

Sources & evidence

ORD record
ord-e861f051886d42ada6169219d0f85b15
Source dataset
uspto-grants-2008_08
Patent number
US07414036B2

Reaction notes

Loading…