Methanol → HCID 178418456, compound

HRID 1451306Notes

Reaction equation

HRID 1451306 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]([OH:18])=[C:7]3[C:15](=[O:16])[NH:14][NH:13][C:12](=[O:17])[C:8]3=[N:9][C:10]=2[CH:11]=1.[OH-].[OH:20][CH2:21][CH2:22][N+:23]([CH3:26])([CH3:25])[CH3:24].C1(C)C=CC=CC=1.CO>O>[OH:20][CH2:21][CH2:22][N+:23]([CH3:26])([CH3:25])[CH3:24].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]([OH:18])=[C:7]3[C:15](=[O:16])[NH:14][NH:13][C:12](=[O:17])[C:8]3=[N:9][C:10]=2[CH:11]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 1140TolueneHCID 31255Choline, hydroxideHCID 178418421HCID 178418421, compound

Product 1

HCID 178418456HCID 178418456, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred suspension of 7-chloro-2,3-dihydro-10-hydroxypyridazino[4,5-b]quinoline -1,4-dione (1.00 g, 3.8 mM) in water (40 mL) was added choline hydroxide (0.86 mL, 3.8 mM, 50 weight per cent, aqueous solution). Toluene (250 mL) was added to the resulting solution and the mixture was concentrated using a rotary evaporator. The residue was diluted with toluene (250 mL) and the resulting mixture concentrated again to provide a yellow residue. This residue was stirred for 60 hr with methanol (25 mL) and the resulting suspension was filtered to separate the solids which were washed with methanol (3 mL) and then dried under a stream of nitrogen for 1 hr. Further drying of the solids in vacuo at 100° C. for 20 hr provided (0.76 g, 55%) of the title compound as a yellow powder, mp 267°-269° C. Analysis for C11H5ClN3O3 ·C5H14NO Calculated: C, 52.4; H, 5.22; N, 15.30 Found: C, 52.2; H, 5.22; N, 15.03

Workup

  1. concentrationthe mixture was concentrated
  2. customa rotary evaporator
  3. additionThe residue was diluted with toluene (250 mL)
  4. concentrationthe resulting mixture concentrated again
  5. customto provide a yellow residue
  6. filtrationthe resulting suspension was filtered
  7. customto separate the solids which
  8. washwere washed with methanol (3 mL)
  9. customdried under a stream of nitrogen for 1 hr
  10. customFurther drying of the solids in vacuo at 100° C. for 20 hr

Sources & evidence

ORD record
ord-83bccf9814e348bc9a91763bf1904586
Source dataset
uspto-grants-1997_02
Patent number
US05604227

Reaction notes

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