Methanol → HCID 178515075, compound

HRID 323613Notes

Reaction equation

HRID 323613 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:26])[C:7]3[C:15](=[O:16])[N:14]([C:17]4[CH:22]=[CH:21][C:20]([O:23]C)=[CH:19][CH:18]=4)[N:13]=[C:12]([OH:25])[C:8]=3[NH:9][C:10]=2[CH:11]=1.C(OCC)C.CO>CS(O)(=O)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:26])[C:7]3[C:15](=[O:16])[N:14]([C:17]4[CH:18]=[CH:19][C:20]([OH:23])=[CH:21][CH:22]=4)[N:13]=[C:12]([OH:25])[C:8]=3[NH:9][C:10]=2[CH:11]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 3283Diethyl EtherHCID 178492082HCID 178492082, compound

Product 1

HCID 178515075HCID 178515075, compoundYield 68.9%

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Conditions

Temperature
150 °C

Procedure

7-Chloro-4-hydroxy-2-(4-methoxyphenyl)-1,2,5,10-tetrahydropyridazino[4,5-b]quinoline-1,10-dione (0.800 g, 2.16 mM) was stirred in methanesulfonic acid (16 mL) to give an amber solution. This solution was heated to 150° C. for 6 hours and cooled to room temperature. Addition of ethyl ether (250 mL) and methanol (50 mL) gave a tan precipitate. The solid was collected and washed with methanol/ether to give the title compound (0.530 g, 51%) as a tan powder, mp 316-318° C.; MS(CI): 356 (M+H).

Workup

  1. customto give an amber solution
  2. temperaturecooled to room temperature
  3. customgave a tan precipitate
  4. customThe solid was collected
  5. washwashed with methanol/ether

Sources & evidence

ORD record
ord-c540ffbd2a91409fa4798d2c94f419f3
Source dataset
uspto-grants-2001_04
Patent number
US06214826B1

Reaction notes

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