Hydrochloric Acid → HCID 15390172, compound

HRID 384995Notes

Reaction equation

HRID 384995 reaction equation
[CH3:1][CH:2]([CH3:14])[CH2:3][CH:4]([C:6]1[S:7][CH:8]=[CH:9][C:10]=1[N+:11]([O-])=O)[CH3:5].[Sn](Cl)(Cl)(Cl)Cl.Cl.[OH-].[Na+]>C(O)C>[CH3:1][CH:2]([CH3:14])[CH2:3][CH:4]([C:6]1[S:7][CH:8]=[CH:9][C:10]=1[NH2:11])[CH3:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24287Tin tetrachlorideHCID 49764778HCID 49764778, compound

Product 1

HCID 15390172HCID 15390172, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

After dissolving 0.33 g of 2-(4-methylpentan-2-yl)-3-nitrothiophene in 6 ml of ethanol, 0.88 g of tin chloride (II) and 0.97 g of concentrated hydrochloric acid were added thereto, and the reaction solution was heated to 70° C. and stirred for an hour. After cooling the solution to room temperature, 1 mol/l of an aqueous sodium hydroxide was added thereto, and the solution stirred for five minutes. The resultant was filtered on cellite, and the filterate was extracted with ethyl acetate. The organic layer was washed with 1 mol/l of aqueous sodium hydroxide and saturated saline. Then, the organic layer was dried with magnesium sulfate and concentrated, and then purified by silica gel chromatography (hexane/ethyl acetate=8/1), thereby obtaining 0.11 g of 2-(4-methylpentan-2-yl)-3-aminothiophene (yield: 39.0%).

Workup

  1. additionwere added
  2. temperatureAfter cooling the solution to room temperature
  3. stirringthe solution stirred for five minutes
  4. filtrationThe resultant was filtered on cellite
  5. extractionthe filterate was extracted with ethyl acetate
  6. washThe organic layer was washed with 1 mol/l of aqueous sodium hydroxide and saturated saline
  7. dry with materialThen, the organic layer was dried with magnesium sulfate
  8. concentrationconcentrated
  9. custompurified by silica gel chromatography (hexane/ethyl acetate=8/1)

Sources & evidence

ORD record
ord-09b7e96e57cd403f9f283c08cebda14a
Source dataset
uspto-grants-2013_02
Patent number
US08367846B2

Reaction notes

Loading…