Methanesulfonic Acid → HCID 21997765, compound

HRID 1977198Notes

Reaction equation

HRID 1977198 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][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]=[CH:4][C:5]2[C:6](=[O:24])[C:7]3[C:14](=[O:15])[NH:13][N:16]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[CH:12]([OH:23])[C:8]=3[NH:9][C:10]=2[CH:11]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 15512858HCID 15512858, compound

Product 1

HCID 21997765HCID 21997765, compoundYield 28.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-Chloro-2-anilino-2,3,4,9-tetrahydro-1H-pyrrolo[3,4-b]-quinoline-1,3,9-trione (1.70 g, 5.00 mM) was stirred in methanol (0.85 L), and methanesulfonic acid (85 mL) was added. The yellow suspension was heated to reflux for 16 hours and cooled to room temperature. The resulting mixture was filtered (the filtrate was saved for use in Example 6), and the collected solids were washed with methanol and dried to give 7-chloro-4-hydroxy-3-phenyl-1,2,5,10-tetrahydropyridazino[4,5-b]-quinoline-1,10-dione (0.48 g, 28%) as a yellow powder. This powder was stirred in methanol, and choline hydroxide (45 weight% in methanol, 0.5 mL) was added to give an amber solution. This solution was concentrated and the residue diluted with toluene and concentrated. The residue was diluted with toluene and concentrated two additional times, and the resulting solid residue was triturated with ethanol/toluene (20%, 25 mL) to provide a crystalline solid. The solid was collected to give the title compound (0.49 g, 78%) as a yellow powder, mp 253-257° C.; MS(CI): 340 (M+H).

Workup

  1. temperatureThe yellow suspension was heated
  2. temperatureto reflux for 16 hours
  3. filtrationThe resulting mixture was filtered (the filtrate
  4. washwere washed with methanol
  5. customdried

Sources & evidence

ORD record
ord-aba39ffb2570418e85c3214d81bb0977
Source dataset
uspto-grants-2001_05
Patent number
US06232313B1

Reaction notes

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