HCID 18925402, compound → HCID 18925404, compound

HRID 1289076Notes

Reaction equation

HRID 1289076 reaction equation
[N+:1]([C:4]1[CH:8]=[CH:7][S:6][C:5]=1[C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)([O-])=O>[Fe].C(O)(=O)C>[NH2:1][C:4]1[CH:8]=[CH:7][S:6][C:5]=1[C:9]1[CH:10]=[CH:11][C:12]([Cl:15])=[CH:13][CH:14]=1

Participants

4

Reactant 1

HCID 18925402HCID 18925402, compound

Product 1

HCID 18925404HCID 18925404, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

To 20 ml of acetic acid, 1 g of 3-nitro-2-(4-chlorophenyl)thiophene and 0.93 g of iron powder were added and heated for 2 hours at 60° C. The reaction mixture was filtered through a diatomaceous earth (Celite) layer. Ethyl acetate was added to the filtrate and extracted 5 times with a 5% aqueous hydrogen chloride solution. The aqueous layer was neutralized with sodium hydrogen carbonate and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 0.54 g of the product as an yellow brown crystal. The yield was 62%. 1H-NMR(CDCl3, δ value):3.82(2H, brs), 6.64(1H, d, J=5.1), 7.12(1H, d, J=5.1), 7.34-7.39(2H, m), 7.43-7.48(2H, m)

Workup

  1. filtrationThe reaction mixture was filtered through a diatomaceous earth (Celite) layer
  2. additionEthyl acetate was added to the filtrate
  3. extractionextracted 5 times with a 5% aqueous hydrogen chloride solution
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-2a92a78c2bba40a8944d5cacdaaf4156
Source dataset
uspto-grants-1998_05
Patent number
US05747518

Reaction notes

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