Hydrochloric Acid → 2-Amino-4-chloro-5-fluorobenzaldehyde

HRID 624531Notes

Reaction equation

HRID 624531 reaction equation
[Cl:1][C:2]1[C:9]([F:10])=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([N+:11]([O-])=O)[CH:3]=1.Cl.O>CCO.CC(O)=O.[Fe]>[NH2:11][C:4]1[CH:3]=[C:2]([Cl:1])[C:9]([F:10])=[CH:8][C:5]=1[CH:6]=[O:7]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 591642274-Chloro-5-fluoro-2-nitrobenzaldehyde

Product 1

HCID 857058702-Amino-4-chloro-5-fluorobenzaldehydeYield 90%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

A mixture of 4-chloro-5-fluoro-2-nitrobenzaldehyde (1.50 g, 7.37 mmol), concentrated hydrochloric acid (0.30 ml, 3.68 mmol), and iron (1.32 g, 23.6 mmol) in EtOH (18 mL), AcOH (18 mL), and water (9 mL) was heated to reflux for 30 minutes, then cooled to RT. The resulting suspension was filtered through CELITE™ and the filtrate was then partitioned between EtOAc and water. The layers were separated, the organic layer was washed with saturated aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to give 2-amino-4-chloro-5-fluorobenzaldehyde as a yellow solid (1.15 g, 90% yield). m/z=174 (M+1).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 30 minutes
  3. filtrationThe resulting suspension was filtered through CELITE™
  4. customthe filtrate was then partitioned between EtOAc and water
  5. customThe layers were separated
  6. washthe organic layer was washed with saturated aqueous sodium bicarbonate solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-216ff343d81c47c09d72146603b2b67a
Source dataset
uspto-grants-2016_04
Patent number
US09303028B2

Reaction notes

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