Sodium Azide → 4-azido-1-methyl-3-nitro-1H-quinolin-2-one

HRID 2244817Notes

Reaction equation

HRID 2244817 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](OS(C2C=CC(C)=CC=2)(=O)=O)=[C:4]([N+:23]([O-:25])=[O:24])[C:3]1=[O:26].[N-:27]=[N+:28]=[N-:29].[Na+]>CN(C=O)C>[N:27]([C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[N:2]([CH3:1])[C:3](=[O:26])[C:4]=1[N+:23]([O-:25])=[O:24])=[N+:28]=[N-:29]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 60145177Toluene-4-sulfonic acid 1-methyl-3-nitro-2-oxo-1,2-dihydro-quinolin-4-yl ester

Product 1

HCID 3874734-azido-1-methyl-3-nitro-1H-quinolin-2-oneYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of toluene-4-sulfonic acid 1-methyl-3-nitro-2-oxo-1,2-dihydro-quinolin-4-yl ester (20.0 g, 53.42 mmol) in DMF (70 mL) was treated with a small excess of sodium azide (3.8 g, 59.0 mmol) and stirred at room temp for 17 h. The solvent was evaporated under reduced pressure. Then the reaction mixture was poured into 500 mL of ice water and the resulting precipitate was collected by suction filtration and dried in vacuo. The pure 4-azido-1-methyl-3-nitro-1H-quinolin-2-one was obtained (12.0 g, 92% yield). 1H-NMR (CDCl3): δ 8.16 (d, 1H, J=8.8 Hz), 7.75 (t, 1H, J=7.6 Hz), 7.42 (d, 1H, J=8.4 Hz), 7.36 (t, 1H, J=7.6 Hz), 3.79 (s, 3H). MS: calculated for C10H7N5O3+H 246.1; found: 246.2.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionThen the reaction mixture was poured into 500 mL of ice water
  3. filtrationthe resulting precipitate was collected by suction filtration
  4. customdried in vacuo

Sources & evidence

ORD record
ord-780ea41bfa814b37a8008f1c17089baf
Source dataset
uspto-grants-2010_03
Patent number
US07678909B1

Reaction notes

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