Ammonium Chloride → HCID 23442422, compound

HRID 2119638Notes

Reaction equation

HRID 2119638 reaction equation
[CH3:1][N:2]1[C:14]2[C:13](=[O:15])[C:12]3[CH:11]=[C:10]([CH2:16][C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-])=O)[CH:18]=4)[CH:9]=[CH:8][C:7]=3[NH:6][C:5]=2[CH:4]=[N:3]1.[Cl-].[NH4+]>C(O)C.O.[Fe]>[NH2:23][C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=1)[CH2:16][C:10]1[CH:9]=[CH:8][C:7]2[NH:6][C:5]3[CH:4]=[N:3][N:2]([CH3:1])[C:14]=3[C:13](=[O:15])[C:12]=2[CH:11]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 9923745HCID 9923745, compound

Product 1

HCID 23442422HCID 23442422, compoundYield 88%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 1-methyl-7-(3-nitrobenzyl)-1,4-dihydro-9H-pyrazolo[4,3-b]quinolin-9-one (EXAMPLE 23, step 2, 76 mg, 0.23 mmol), iron powder (63 mg, 1.1 mmol), and ammonium chloride (12 mg, 0.023 mmol) in ethanol (15 ml) and water (5 ml) was refluxed for 2 h. After cooling to room temperature, the mixture was filtered through a pad of Celite and the filtrate was concentrated in vacuo. The residue was collected by filtration and washed with ethanol and diisopropyl ether to give 60 mg (88%) of 7-(3-aminobenzyl)-1-methyl-1,4-dihydro-9H-pyrazolo[4,3-b]quinolin-9-one. 24 mg of this solid was treated with methanolic hydrochloric acid and the mixture was evaporated. The residue was washed with diisopropyl ether to give 29 mg of the title compound as a white solid.

Workup

  1. temperaturewas refluxed for 2 h
  2. filtrationthe mixture was filtered through a pad of Celite
  3. concentrationthe filtrate was concentrated in vacuo
  4. filtrationThe residue was collected by filtration
  5. washwashed with ethanol and diisopropyl ether

Sources & evidence

ORD record
ord-40fdb628c4c4438989b6cf2de5ecaee6
Source dataset
uspto-grants-2004_02
Patent number
US06686373B2

Reaction notes

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