Sulfuric Acid → HCID 22492680, compound

HRID 1939117Notes

Reaction equation

HRID 1939117 reaction equation
[CH2:1]([C:11]1[C:16](N)=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[N+:18]([C:21]1C=C(S(O)(=O)=O)C=[CH:25][CH:26]=1)([O-])=O.S(=O)(=O)(O)O.B(O)(O)O>OCC(CO)O.[Fe]=S.O>[CH2:1]([C:11]1[CH:16]=[C:15]2[C:14](=[CH:13][CH:12]=1)[N:18]=[CH:21][CH:26]=[CH:25]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 73873-Nitrobenzenesulfonic acidHCID 7628Boric AcidHCID 14619438HCID 14619438, compound

Product 1

HCID 22492680HCID 22492680, compoundYield 30.2%

Reagents, catalysts & solvents 3

HCID 14828Ferrous sulfideCatalystHCID 753GlycerolSolventHCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

12.5 g of 6-decylaniline, 5.0 g of 3-nitrobenzenesulfonic acid, 1.5 g of iron (II) sulfide, 10 ml of sulfuric acid, and 2.8 g of boric acid were dissolved in 13 ml of glycerin (glycerol), followed by stirring for 6 hours at 140° C. After the reaction, the reaction mixture was poured into water and alkalinized by adding thereto an appropriately amount of sodium hydroxide aqueous solution, followed by extraction with diethyl ether. The organic layer was washed with water, dried with anhydrous sodium sulfate and subjected to distilling-off of the solvent, followed by purification by silica gel column chromatography to obtain 2.0 g of 6-decylquinoline.

Workup

  1. customAfter the reaction
  2. additionby adding
  3. extractionan appropriately amount of sodium hydroxide aqueous solution, followed by extraction with diethyl ether
  4. washThe organic layer was washed with water
  5. dry with materialdried with anhydrous sodium sulfate
  6. customfollowed by purification by silica gel column chromatography

Sources & evidence

ORD record
ord-ffc6bd5646a241e5b8edad66128785dd
Source dataset
uspto-grants-1997_12
Patent number
US05695684

Reaction notes

Loading…