Diethyl Ether → HCID 178515074, compound

HRID 1600030Notes

Reaction equation

HRID 1600030 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:26])[C:7]3[C:15]([OH:16])=[N:14][N:13]([C:17]4[CH:22]=[CH:21][C:20]([O:23]C)=[CH:19][CH:18]=4)[C:12](=[O:25])[C:8]=3[NH:9][C:10]=2[CH:11]=1.C(OCC)C>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]([OH:16])=[N:14][N:13]([C:17]4[CH:18]=[CH:19][C:20]([OH:23])=[CH:21][CH:22]=4)[C:12](=[O:25])[C:8]=3[NH:9][C:10]=2[CH:11]=1

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 178492080HCID 178492080, compound

Product 1

HCID 178515074HCID 178515074, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Conditions

Temperature
160 °C

Procedure

7-Chloro-1-hydroxy-3-(4-methoxyphenyl)-3,4,5,10-tetrahydropyridazino[4,5-b]-quinoline-4,10-dione (0.800 g, 2.16 mM) was stirred in methanesulfonic acid (16 mL) to give an amber solution. This solution was heated to 160° C. for 6 hours and cooled to room temperature. Addition of ethyl ether (250 mL) gave a tan precipitate which was stirred for 1 hour. The solid was collected and washed with methanol/ether to give the title compound (0.661 g, 77%) as a tan powder, mp 393°-395° C.; MS(CI): 356 (M+H). Analysis for C17H10CNl3O4 ·0.2CH3SO3H·1.3 H2O: Calculated: C, 51.86; H, 3.39; N, 10.55; Found: C, 51.76; H, 3.02; N, 10.37; NMR: 13.30 (s, 1H, exchangeable), 12.5 (v br s, 1H, exchangeable), 10.8 (br s, 1H, exchangeable), 8.29 (d, J=8.76 Hz, 1H,), 8.23 (br s, 1H), 7.61 (br d, J=8.76 Hz, 1H,), 7.45 (d, J=8.81 Hz, 2H), 6.88 (d, J=8.81 Hz, 2H), 2.32 (s, 0.5H).

Workup

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

Sources & evidence

ORD record
ord-063f13ac797b4a049b5f304b0b1db953
Source dataset
uspto-grants-1998_04
Patent number
US05744471

Reaction notes

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