Hydrazine hydrate (1:1) → HCID 19592299, compound

HRID 613559Notes

Reaction equation

HRID 613559 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([NH:12][C:13](=[O:22])[C:14]3[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:21])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[CH2:23][OH:24].O.[NH2:26][NH2:27]>CN1CCCC1=O.C(OCC)(=O)C>[Cl:21][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]([Cl:20])[C:14]=1[C:13]([NH:12][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[N:5]=[CH:4][C:3]([CH2:23][OH:24])=[C:2]2[NH:26][NH2:27])=[O:22].[Cl:21][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]([Cl:20])[C:14]=1[C:13]([NH:12][C:7]1[C:6]2[N:5]=[CH:4][C:3]3[CH:23]=[N:26][NH:27][C:2]=3[C:11]=2[CH:10]=[CH:9][CH:8]=1)=[O:22]

Participants

6

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 19592338HCID 19592338, compound

Product 2

HCID 19592299HCID 19592299, compoundHCID 19592809HCID 19592809, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 4-chloro-8-(2,6-dichlorobenzoylamino)-3-hydroxymethylquinoline (297 mg) in N-methylpyrrolidone (4 ml) was added hydrazine monohydrate (390 mg), and the mixture was stirred for 3 hours at 90° C. The mixture was diluted with ethyl acetate, washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by flash chromatography on silica gel and by preparative thin layer chromatography to give 8-(2,6-dichlorobenzoylamino)-4-hydrazino-3-hydroxymethylquinoline (127 mg) and 6-(2,6-dichlorobenzoylamino)-1H-pyrazolo[4,3-c]-quinoline (90 mg). 8-(2,6-Dichlorobenzoylamino)-4-hydrazino-3-hydroxymethylquinoline NMR (DMSO-d6, δ): 4.70 (2H, d, J=6 Hz), 5.19 (2H, s), 5.35 (1H, t, J=6 Hz), 7.39 (1H, dd, J=8, 8 Hz), 7.49-7.63 (3H, m), 8.15 (1H, d, J=8 Hz), 8.28 (1H, s), 8.40 (1H, s), 8.56 (1H, d, J=8 Hz), 10.46 (1H, s) 6-(2,6-Dichlorobenzoylamino)-1H-pyrazolo[4,3-c]quinoline NMR (DMSO-d6, δ): 7.49-7.63 (3H, m), 7.77 (1H, dd, J=8, 8 Hz), 8.20 (1H, d, J=8 Hz), 8.46 (1H, br s), 8.78 (1H, d, J=8 Hz), 9.25 (1H, s), 10.76 (1H, s)

Workup

  1. washwashed with water and brine
  2. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was purified by flash chromatography on silica gel and by preparative thin layer chromatography

Sources & evidence

ORD record
ord-00ab68a963354baf82191aeb539232e5
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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