Ammonium Sulfite → 2-Amino-6-bromonaphthalene

HRID 1642353Notes

Reaction equation

HRID 1642353 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7](O)[CH:6]=[CH:5]2.S([O-])([O-])=O.[NH4+:17].[NH4+]>N>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([NH2:17])[CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 25041Ammonium SulfiteHCID 271446-Bromo-2-naphthalenol

Product 1

HCID 3484042-Amino-6-bromonaphthaleneYield 33.5%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Conditions

Temperature
190 °C

Procedure

6-Bromo-2-naphthol (2.0 g, 9 mmol), ammonium sulfite (10.4 g, 90 mmol) and 10 mL of ammonia solution were sealed in a tube. The reaction mixture was heated at 190° C. for 24 hrs and allowed to cool to room temperature, the reaction mixture was extracted with EtOAc. HCl (10%) was added to the organic layer to give a precipitate. After filtration, the solid was dissolved in 10% of Na2CO3 and extracted with EtOAc, the organic layer was dried over Na2SO4. The solvent was removed under reduced pressure to give the product as yellow solid (0.67 g, 33%). MS[M++43]=265, LC-MS: tR=2.14 min.

Workup

  1. temperatureto cool to room temperature
  2. extractionthe reaction mixture was extracted with EtOAc
  3. additionHCl (10%) was added to the organic layer
  4. customto give a precipitate
  5. filtrationAfter filtration
  6. dissolutionthe solid was dissolved in 10% of Na2CO3
  7. extractionextracted with EtOAc
  8. dry with materialthe organic layer was dried over Na2SO4
  9. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-0c15e41a44f6414eb1f0f25e49337d4b
Source dataset
uspto-grants-2012_02
Patent number
US08119660B2

Reaction notes

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