Ethanol → HCID 23442320, compound

HRID 2119650Notes

Reaction equation

HRID 2119650 reaction equation
[Cl:1][C:2]1[C:11]2[C:10]([C:12]3[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=3)=[CH:9][CH:8]=[CH:7][C:6]=2[N:5]=[C:4]2[CH:21]=[N:22][N:23]([CH3:24])[C:3]=12.[Cl-].[NH4+].C([OH:29])C>O.[Fe]>[ClH:1].[NH2:18][C:15]1[CH:16]=[CH:17][C:12]([C:10]2[C:11]3[C:2](=[O:29])[C:3]4[N:23]([CH3:24])[N:22]=[CH:21][C:4]=4[NH:5][C:6]=3[CH:7]=[CH:8][CH:9]=2)=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 23442389HCID 23442389, compound

Product 1

HCID 23442320HCID 23442320, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

A mixture of 9-chloro-1-methyl-8-(4-nitrophenyl)-1H-pyrazolo[4,3-b]quinoline (EXAMPLE 41, step 1, 45 mg, 0.13 mmol), iron powder (37 mg, 0.67 mmol) and ammonium chloride (0.7 mg, 0.013 mmol) in a mixture of ethanol (4 ml) and water (1.5 ml) was refluxed for 8 h. After cooling to room temperature, the mixture was filtered through a pad of Celite. The filtrate was concentrated, dissolved in ethyl acetate (300 ml), washed with water (100 ml) and dried over magnesium sulfate. Removal of solvent gave 41 mg (99%) of the title compound as a solid.

Workup

  1. temperaturewas refluxed for 8 h
  2. filtrationthe mixture was filtered through a pad of Celite
  3. concentrationThe filtrate was concentrated
  4. dissolutiondissolved in ethyl acetate (300 ml)
  5. washwashed with water (100 ml)
  6. dry with materialdried over magnesium sulfate
  7. customRemoval of solvent

Sources & evidence

ORD record
ord-8e8becf628054d18ae48dbfde18bc1da
Source dataset
uspto-grants-2004_02
Patent number
US06686373B2

Reaction notes

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