4-Fluoroaniline → 7-FLUORO-1-METHYL-1,4-DIHYDRO-9H-PYRAZOLO[4,3-b]QUINOLIN-9-ONE

HRID 2119615

반응식

HRID 2119615 반응식
I[C:2]1[CH:3]=[N:4][N:5]([CH3:10])[C:6]=1[C:7](O)=[O:8].[F:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Na+].[Na+].[OH-].[Na+]>[Cu].C(OCC)C>[F:11][C:12]1[CH:18]=[CH:17][C:15]2[NH:16][C:2]3[CH:3]=[N:4][N:5]([CH3:10])[C:6]=3[C:7](=[O:8])[C:14]=2[CH:13]=1

참가 물질

7

반응물 4

HCID 97314-FluoroanilineHCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 6736874-Iodo-1-methyl-1H-pyrazole-5-carboxylic acid

생성물 1

HCID 129856947-FLUORO-1-METHYL-1,4-DIHYDRO-9H-PYRAZOLO[4,3-b]QUINOLIN-9-ONE수율 61%

시약·촉매·용매 2

HCID 23978Copper촉매HCID 3283Diethyl Ether용매

실험 절차

A mixture of 4-iodo-1-methyl-1H-pyrazole-5-carboxylic acid ((Manaev, Yu. A. et al., J. Gen. Chem. USSR (Engl. Transl.), 1982, 52 (11), 2291), 500 mg, 1.98 mmol), 4-fluoroaniline (0.94 ml, 9.90 mmol), copper powder (200 mg) and 5% aqueous sodium carbonate (10 ml) was stirred for 16 h at 100° C. After cooling to room temperature, 2N aqueous sodium hydroxide (100 ml) and diethyl ether (50 ml) were added to the mixture. The mixture was filtered through a pad of Celite. The water layer was separated, washed with diethyl ether (50 ml) and acidified with concentrated hydrochloric acid. The formed precipitate was collected by filtration and dried to give 282 mg (61%) of the title compound as a white solid.

후처리

  1. filtrationThe mixture was filtered through a pad of Celite
  2. customThe water layer was separated
  3. washwashed with diethyl ether (50 ml)
  4. filtrationThe formed precipitate was collected by filtration
  5. customdried

출처 및 근거

ORD 기록
ord-61298bab12dd4f30a5a7fed1e8a287bf
출처 데이터셋
uspto-grants-2004_02
특허 번호
US06686373B2

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