Sodium Azide → 3-Methoxyaniline

HRID 1481675Notes

Reaction equation

HRID 1481675 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]2C(C(=O)NC3C=CC=CC=3)=CN=C(S(C)(=O)=O)N=2)[CH:9]=1)(C)(C)C.[N-]=[N+]=[N-].[Na+]>CN(C=O)C>[CH3:15][O:14][C:10]1[CH:9]=[C:8]([CH:13]=[CH:12][CH:11]=1)[NH2:7]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 59174704HCID 59174704, compound

Product 1

HCID 108243-MethoxyanilineYield 353%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 7 (0.4 g, 0.69 mmol) in DMF (5 mL) was added sodium azide (0.054 g, 0.83 mmol) and the reaction mixture was heated to 70° C. for 4 h. Then it was treated with ice water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and with brine, dried over anhydrous Na2SO4, filtered and concentrated to obtain 8 as viscous oil 8 (0.3 g, 82.6%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water and with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-79c52d3048c24a2a829cbd04ef5b13eb
Source dataset
uspto-grants-2016_08
Patent number
US09409921B2

Reaction notes

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