HCID 60046932, compound → HCID 60046926, compound

HRID 1672310Notes

Reaction equation

HRID 1672310 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)=[C:7]([N+:12]([O-])=O)[CH:8]=[N:9]2)=[CH:4][CH:3]=1>C1COCC1.CO.[Ni]>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)=[C:7]([NH2:12])[CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 60046932HCID 60046932, compound

Product 1

HCID 60046926HCID 60046926, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

1.3 g (4.09 mmol) (7-chloro-3-nitro-quinolinyl)-(4-fluoro-phenyl)-amine (Example 15c) in 60 ml THF/MeOH 2:1 and 0.6 g Raney-Ni are hydrogenated at rt for 2 h. The reaction solution is filtered on Hyflo® Super Cel diatomaceous earth and is evaporated to dryness. The raw product is dissolved in 30 ml ethyl acetate, and ca. 400 ml hexane are added. The title compound precipitates and is collected by filtration. Drying follows at 65° C. over night. mp: 198-200° C.; MS: 288 (M++1); HPLC: tret=8.38 min (Grad 1).

Workup

  1. filtrationThe reaction solution is filtered on Hyflo® Super Cel diatomaceous earth
  2. customis evaporated to dryness
  3. dissolutionThe raw product is dissolved in 30 ml ethyl acetate
  4. additionca. 400 ml hexane are added
  5. customThe title compound precipitates
  6. filtrationis collected by filtration
  7. customDrying
  8. waitfollows at 65° C. over night
  9. customtret=8.38 min (Grad 1)

Sources & evidence

ORD record
ord-6f10e01e9c58416595f962f1bd2d17a4
Source dataset
uspto-grants-2011_08
Patent number
US07998972B2

Reaction notes

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