Sodium Hydroxide → HCID 22406556, compound

HRID 440273Notes

Reaction equation

HRID 440273 reaction equation
[N+:1]([C:4]1[S:5][CH:6]=[C:7]([C:9]([O:11][CH2:12][CH:13]=[CH2:14])=[O:10])[CH:8]=1)([O-])=O.O.O.Cl[Sn]Cl.[OH-].[Na+]>Cl>[NH2:1][C:4]1[S:5][CH:6]=[C:7]([C:9]([O:11][CH2:12][CH:13]=[CH2:14])=[O:10])[CH:8]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 22406568HCID 22406568, compound

Product 1

HCID 22406556HCID 22406556, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Allyl 2-nitro-4-thiophenecarboxylate was suspended in concentrated HCl (25 ml), at 0°. SnCl2.2H2O (7.44 g, 32.36 mmol) was added and after stirring for 4 hours at ambient temperature the pH was adjusted to 10 with NaOH. Extraction with ethyl acetate and purification by subjecting to flash silica gel chromatography using ethyl acetate/petroleum ether as eluant (25:75), gave the title compound (1.15 g, 55%).

Workup

  1. extractionExtraction
  2. customwith ethyl acetate and purification

Sources & evidence

ORD record
ord-3d1d6fa1850b44748b5f2552211d6e87
Source dataset
uspto-grants-1996_05
Patent number
US05519015

Reaction notes

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