Sodium hydrosulfide → 7-Nitro-2-aminonaphthalene

HRID 1270753Notes

Reaction equation

HRID 1270753 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][C:8]([N+:14]([O-])=O)=[CH:9][CH:10]=2)[CH:5]=1)([O-:3])=[O:2].[SH-].[Na+]>CO.O>[N+:1]([C:4]1[CH:5]=[C:6]2[C:11]([CH:10]=[CH:9][C:8]([NH2:14])=[CH:7]2)=[CH:12][CH:13]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 28015Sodium hydrosulfideHCID 906202,7-Dinitronaphthalene

Product 1

HCID 154071007-Nitro-2-aminonaphthalene

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

To a solution of 2,7-dinitronaphthalene (500 mg, 2.29 mmol) in methanol (5 mL) heated to reflux, is added over 15 minutes, a solution of sodium hydrosulfide (196 mg, 3.44 mmol) in methanol (5 mL) and water (10 mL). The reaction mixture is heated at reflux for 30 minutes and then poured into ice-water and filtered to give an orange solid. After washing the solid with boiling 10% aqueous HCl, the filtrate is basified with solid NaOH and extracted with EtOAc. The organic layer is dried (Na2SO4) and the solvents are evaporated to give 7-nitro-2-aminonaphthalene as a bright orange solid.

Workup

  1. temperatureto reflux
  2. additionis added over 15 minutes
  3. temperatureThe reaction mixture is heated
  4. temperatureat reflux for 30 minutes
  5. filtrationfiltered
  6. customto give an orange solid
  7. washAfter washing the solid
  8. extractionextracted with EtOAc
  9. dry with materialThe organic layer is dried (Na2SO4)
  10. customthe solvents are evaporated

Sources & evidence

ORD record
ord-2786d630c60a4e2f9488ee3d2613fc01
Source dataset
uspto-grants-2007_04
Patent number
US07202364B2

Reaction notes

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