Isatoic Anhydride → N-propylisatoic anhydride

HRID 53256

Reaction equation

HRID 53256 reaction equation
[C:1]12[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:6][C:5](=[O:12])[O:4][C:2]2=[O:3].[CH2:13](I)[CH2:14][CH3:15].[H-].[Na+]>>[CH2:13]([N:6]1[C:5](=[O:12])[O:4][C:2](=[O:3])[C:1]2=[CH:11][CH:10]=[CH:9][CH:8]=[C:7]12)[CH2:14][CH3:15]

Participants

4

Reactant 3

HCID 8359Isatoic AnhydrideHCID 24758Sodium hydrideHCID 336431-Iodopropane

Product 1

HCID 3933296N-propylisatoic anhydride

Procedure

To a stirred solution of isatoic anhydride (100 g) and propyl iodide (66 ml) in dimethylfomamide (600 ml) at 0° C., under nitrogen, was added sodium hydride (28 g of a 55% dispersion in mineral oil) portionwise. The mixture was allowed to warm to room temperature and stirred for 18 h. The solvent was then removed in vacuo and the residue partitioned between ethyl acetate (1000 ml) and water (500 ml). The organic phase was separated, washed with brine (2×500 ml), dried (MgSO4) and evaporated. The residue was triturated with anhydrous diethyl ether to give the title compound (57 g). 1H NMR (360 MHz, CDCl3) δ1.06 (3H, t, J=7.5 Hz), 1.75-1.86 (2H, m), 4.01-4.05 (2H, m), 7.17 (1H, d, J=8.5 Hz), 7.26-7.32 (1H, m), 7.73-7.78 (1H, m), 8.17 (1H, dd, J=7.9 and 1.7 Hz). MS (CI) m/e 205 [MH]+.

Workup

  1. customThe solvent was then removed in vacuo
  2. customthe residue partitioned between ethyl acetate (1000 ml) and water (500 ml)
  3. customThe organic phase was separated
  4. washwashed with brine (2×500 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue was triturated with anhydrous diethyl ether

Sources & evidence

ORD record
ord-0432be68ecb348b0a5947b64efdfec62
Source dataset
uspto-grants-1997_04
Patent number
US05618812

Linked notes

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