Methanesulfonic Acid → HCID 178515071, compound

HRID 323627Notes

Reaction equation

HRID 323627 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:28])[C:7]3[C:14](=[O:15])[N:13]([NH:16][C:17]4[C:26]5[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=5)[CH:20]=[CH:19][CH:18]=4)[C:12](=[O:27])[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:28])[C:7]3[C:14]([OH:15])=[N:13][N:16]([C:17]4[C:18]5[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=5)[CH:24]=[CH:25][CH:26]=4)[C:12](=[O:27])[C:8]=3[NH:9][C:10]=2[CH:11]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 15512861HCID 15512861, compound

Product 1

HCID 178515071HCID 178515071, compoundYield 43.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-Chloro-2-(1-naphthylamino)-2,3,4,9-tetrahydro-1H-pyrrolo[3,4-b]quinoline-1,3,9-trione (1.30 g, 3.34 mM) was stirred in methanol (0.65 L) and methanesulfonic acid (65 mL) was added. The brown suspension was heated to reflux for 16 hours during which the solids dissolved to give a brown solution. This solution was cooled to room temperature. Addition of ice (10 mL) gave a tan suspension which was stirred for 1.5 hours. The suspension was filtered (the filtrate was saved for use in Example 24) and the collected solids were washed with methanol and ether to give the title compound (0.560 g, 43%) as a dull yellow powder, mp 374-376° C.; MS(CI): 390 (M+H).

Workup

  1. temperatureThe brown suspension was heated
  2. temperatureto reflux for 16 hours during which the solids
  3. dissolutiondissolved
  4. customto give a brown solution
  5. customgave a tan suspension which
  6. filtrationThe suspension was filtered (the filtrate
  7. washwere washed with methanol and ether

Sources & evidence

ORD record
ord-f00ab75a832d4853be67a3e43b2f4cbd
Source dataset
uspto-grants-2001_04
Patent number
US06214826B1

Reaction notes

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