Hydrochloric Acid → 2-Aminobenzaldehyde

HRID 2276343Notes

Reaction equation

HRID 2276343 reaction equation
Cl.[N+:2]([C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH:7]=[O:8])([O-])=O.C(O)C>[Fe].O>[NH2:2][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH:7]=[O:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 111012-Nitrobenzaldehyde

Product 1

HCID 682552-AminobenzaldehydeYield 96.7%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

Iron powder (39 g; 700 mmol) and concentrated hydrochloric acid (0.583 mL; 7 mmol) were added to a solution of 2-nitrobenzaldehyde (10.58 g; 70 mmol) in a mixture ethanol (210 mL)-water (52 mL). The well-stirred reaction mixture was heated to reflux for 5 h. After cooling, the suspension was filtered on a plug of celite, washed with ethanol and the filtrate was concentrated under reduced pressure until the organics were removed. The remaining aqueous layer was extracted with ethyl acetate, the organics were combined, dried over sodium sulfate, concentrated under reduced pressure to furnish 8.2 g (96%) of 2-aminobenzaldehyde as a yellow oil, which crystallized slowly. ESI/APCI(+): 122 (M+H). NMR 1H (CDCl3) (ppm): δ 9.87 (s, 1H, CHO); 7.48 (dd, 1H, Harom.); 7.31 (td, 1H, Harom.); 6.75 (td, 1H, Harom.); 6.51 (dd, 1H, Harom.); 6.11 (bs, 2H, NH2).

Workup

  1. customThe well-stirred reaction mixture
  2. temperaturewas heated
  3. temperatureto reflux for 5 h
  4. temperatureAfter cooling
  5. filtrationthe suspension was filtered on a plug of celite
  6. washwashed with ethanol
  7. concentrationthe filtrate was concentrated under reduced pressure until the
  8. customorganics were removed
  9. extractionThe remaining aqueous layer was extracted with ethyl acetate
  10. dry with materialdried over sodium sulfate
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-31b41c6e26bb4d0daadb461d6a5e7337
Source dataset
uspto-grants-2015_09
Patent number
US09132129B2

Reaction notes

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