Hydrochloric Acid → 1-Methyl-7-nitroisatoic anhydride

HRID 1879587Notes

Reaction equation

HRID 1879587 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:7]=[C:8]2[NH:14][C:13](=[O:15])[O:12][C:10](=[O:11])[C:9]2=[CH:16][CH:17]=1)([O-:5])=[O:4].[CH3:18]I.Cl>CN(C=O)C>[CH3:18][N:14]1[C:13](=[O:15])[O:12][C:10](=[O:11])[C:9]2[CH:16]=[CH:17][C:6]([N+:3]([O-:5])=[O:4])=[CH:7][C:8]1=2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 2820894-Nitro-isatoic anhydride

Product 1

HCID 125353731-Methyl-7-nitroisatoic anhydrideYield 86.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 0.1656 g (4.14 mmoles) of sodium hydride (60% in mineral oil) in 20 mL DMF was added a solution of 0.6584 g (3.16 mmoles) of 4-nitroisatoic anhydride in 20 mL DMF. After stirring a few minutes at room temperature, a clear orange solution formed. 0.2615 g (3.2 mmoles) of methyl iodide was added to the reaction, and the mixture was stirred at room temperature for 4 hours. The reaction was poured into 50 mL of cold 1 N HCl, and the resulting bright orange precipitate was filtered and washed sequentially with water and ether to give 608.3 mg (86%) of product. 1H NMR (CO(CD3)2, 400 MHz,) δ 3.69 (s, 3H, —NCH3—), 8.12 (dd, J=8.8 Hz, 2 Hz, 1H, ArH), 8.2 (d, J=2 Hz, 1H, ArH), 8.34 (d, J=8.4 Hz, 1H, ArH).

Workup

  1. customa clear orange solution formed
  2. stirringthe mixture was stirred at room temperature for 4 hours
  3. filtrationthe resulting bright orange precipitate was filtered
  4. washwashed sequentially with water and ether

Sources & evidence

ORD record
ord-5b06c20a903240cfb9797732cd4237f8
Source dataset
uspto-grants-2012_11
Patent number
US08318424B2

Reaction notes

Loading…