Methanesulfonic Acid → HCID 178515132, compound

HRID 323625Notes

Reaction equation

HRID 323625 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([Cl:25])[C:5]2[C:6](=[O:24])[C:7]3[C:14](=[O:15])[N:13]([NH:16][C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:12](=[O:23])[C:8]=3[NH:9][C:10]=2[CH:11]=1.CS(O)(=O)=O>CO>[Cl:1][C:2]1[CH:3]=[C:4]([Cl:25])[C:5]2[C:6](=[O:24])[C:7]3[C:14](=[O:15])[N:16]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[N:13]=[C:12]([OH:23])[C:8]=3[NH:9][C:10]=2[CH:11]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 219977166,8-Dichloro-2-anilino-2,3,4,9-tetrahydro-1H-pyrrolo[3,4-b]quinoline-1,3,9-trione

Product 1

HCID 178515132HCID 178515132, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6,8-Dichloro-2-anilino-2,3,4,9-tetrahydro-1H-pyrrolo[3,4-b]quinoline-1,3,9-trione (0.60 g, 1.60 mM) was stirred in methanol (200 mL) and methanesulfonic acid (20 mL) was added with cooling, maintaining the temperature below 20° C. The resulting orange solution was stirred overnight at room temperature. A precipitate formed overnight and the orange suspension was heated to reflux for 1 hour. The suspension was cooled to room temperature and allowed to stand overnight without stirring. The suspension was filtered and the filtrates were slowly diluted with water (200 mL) to give a yellow suspension. This suspension was stirred for two hours and the solids were collected and washed with water, aqueous methanol, 50% methanol/ether, and ether to give the title compound (0.368 g, 61%) as a light tan powder, mp 361-363° C.; MS(CI): 374 (M+H).

Workup

  1. temperaturewith cooling
  2. temperaturemaintaining the temperature below 20° C
  3. customA precipitate formed overnight
  4. temperaturethe orange suspension was heated
  5. temperatureto reflux for 1 hour
  6. temperatureThe suspension was cooled to room temperature
  7. waitto stand overnight
  8. stirringwithout stirring
  9. filtrationThe suspension was filtered
  10. additionthe filtrates were slowly diluted with water (200 mL)
  11. customto give a yellow suspension
  12. stirringThis suspension was stirred for two hours
  13. customthe solids were collected
  14. washwashed with water, aqueous methanol, 50% methanol/ether, and ether

Sources & evidence

ORD record
ord-341d43abf5a7425ab3e4ee7c1215dc45
Source dataset
uspto-grants-2001_04
Patent number
US06214826B1

Reaction notes

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