Acetic Anhydride → 5,7-Dichloro-1,2,3,4-tetrahydroquinoline-2,3,4-trione-3-acetyloxime

HRID 2259625Notes

Reaction equation

HRID 2259625 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]2[C:3]=1[C:4](=[O:16])[C:5](=[N:14][OH:15])[C:6](=[O:13])[NH:7]2.[C:17](OC(=O)C)(=[O:19])[CH3:18]>CS(C)=O>[C:17]([O:15][N:14]=[C:5]1[C:4](=[O:16])[C:3]2[C:8](=[CH:9][C:10]([Cl:12])=[CH:11][C:2]=2[Cl:1])[NH:7][C:6]1=[O:13])(=[O:19])[CH3:18]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 178517235HCID 178517235, compound

Product 1

HCID 539062125,7-Dichloro-1,2,3,4-tetrahydroquinoline-2,3,4-trione-3-acetyloximeYield 97%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 201 mg (0.776 mmole) of 17b in 2 mL of DMSO was added 0.4 mL of acetic anhydride and the solution was stirred overnight. Solid precipitate was observed after about 1 hr. To the mixture was added 10 mL of ice-water and the mixture was stirred until all of the ice melted. The mixture was filtered and washed with water, and dried to leave 228 mg (97%) of 18b as a yellow solid, mp 194°-195° C. 1H NMR (DMSO-d6), 2.292 (s, 3), 7.095 (m, 1), 7.34 (m, 1), 11.39 (s, 0.4), 11.51 (s, 0.6).

Workup

  1. waitSolid precipitate was observed after about 1 hr
  2. filtrationThe mixture was filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-a3ab3db3dc2d49adbc7eadfa9d41e24f
Source dataset
uspto-grants-1995_12
Patent number
US05475007

Reaction notes

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