HCID 15224452, compound → HCID 15224453, compound

HRID 1699713Notes

Reaction equation

HRID 1699713 reaction equation
[Cl:1][C:2]1[C:11]([N+:12]([O-])=O)=[C:10]([NH:15][CH2:16][C:17]([CH3:21])([OH:20])[CH:18]=[CH2:19])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1>[Pt].C(O)C>[NH2:12][C:11]1[C:2]([Cl:1])=[N:3][C:4]2[C:9]([C:10]=1[NH:15][CH2:16][C:17]([CH2:18][CH3:19])([CH3:21])[OH:20])=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

4

Reactant 1

HCID 15224452HCID 15224452, compound

Product 1

HCID 15224453HCID 15224453, compoundYield 67.4%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

4-[(2-Chloro-3-nitro-4-quinolinyl)amino]-3-methyl-1-butene-3-ol (10.8 g, 0.035 mole, Example 118) was combined with ethanol (300 mL) and 0.5 g 5% platinum on carbon. The mixture was hydrogenated on a Parr apparatus. The reaction mixture was filtered through celite and the filtrate was concentrated to provide an oil. The oil was purified by silica gel column chromatography. An attempt to crystallize the purified oil using ethanol and water produced an oil. The mixture was concentrated under vacuum with toluene then extracted with methylene chloride. The methylene chloride extract was dried over magnesium sulfate then concentrated under vacuum to provide 6.6 g of the desired product as a solid, m.p. 99-101° C. Analysis: Calculated: %C, 60.1; %H, 6.5; %N, 15.0; Found: %C, 60.0; %H, 6.4; %N, 14.8.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated
  3. customto provide an oil
  4. customThe oil was purified by silica gel column chromatography
  5. customAn attempt to crystallize the purified oil
  6. customproduced an oil
  7. concentrationThe mixture was concentrated under vacuum with toluene
  8. extractionthen extracted with methylene chloride
  9. extractionThe methylene chloride extract
  10. dry with materialwas dried over magnesium sulfate
  11. concentrationthen concentrated under vacuum

Sources & evidence

ORD record
ord-be4f7378c6024273aa6c0c3da81cf3ba
Source dataset
uspto-grants-2002_02
Patent number
US06348462B1

Reaction notes

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