Sodium Azide → 6-Methoxynaphthalen-2-amine

HRID 2214336Notes

Reaction equation

HRID 2214336 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8](C(O)=O)[CH:7]=[CH:6]2.[N-:16]=[N+]=[N-].[Na+]>C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([NH2:16])[CH:7]=[CH:6]2

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 3491816-Methoxy-2-Naphthoic Acid2×

Product 1

HCID 124051106-Methoxynaphthalen-2-amine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

To a 50 ml two-necked flask, 1.0 g (3.5 mmol) of 6-methoxynaphthalene-2-carboxylic acid (Compound 1), 2.28 g (35.0 mmol) of sodium azide and 15.0 g of polyphosphoric acid (PPA) were added, and the mixture was stirred at 40° C. for 12 hours. To the resulting mixture, 100 g of ethyl acetate was added and the obtained mixture was washed with saturated aqueous sodium hydrogen carbonate, followed by drying the product over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to obtain the desired compound.

Workup

  1. washthe obtained mixture was washed with saturated aqueous sodium hydrogen carbonate
  2. dry with materialby drying the product over anhydrous sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7e515d420e46454f85dad61da5c2b20a
Source dataset
uspto-grants-2006_09
Patent number
US07109043B2

Reaction notes

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