Methane → HCID 14986960, compound

HRID 1292475Notes

Reaction equation

HRID 1292475 reaction equation
O[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].ClCCl.P(Cl)(Cl)(Cl)=O.[CH4:23]>C(OCC)C.CN(C)C=O>[CH3:23][C:6]([NH:5][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13])([CH3:11])[CH3:7]

Participants

7

Reactant 4

HCID 297MethaneHCID 6344DichloromethaneHCID 24813Phosphorus oxychlorideHCID 178526762HCID 178526762, compound

Product 1

HCID 14986960HCID 14986960, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 19 g (0.10 mole) of 4-hydroxy-3-nitroquinoline, 200 mL of dichloromethane, 10 mL of N,N-dimethylformamide and 10 mL of phosphorus oxychloride was stirred at about 20° C. for 30 minutes and then heated at its reflux temperature for 30 minutes. The solution was cooled to about 20° C. and diluted with 300 mL of diethyl ether. This solution was stirred for 30 minutes at 20° C., treated with decolorizing charcoal and filtered through celite. The filtrate was washed repeatedly with 200 mL portions of cold sodium bicarbonate solution until foaming stopped and the washings were basic. The solution containing 4-chloro-3-nitroquinoline was dried over magnesium sulfate and filtered and evaporated in vacuo. To the solid was added a mixture of 20 g of tertiary-butylamine and 100 mL of N,N-dimethylformamide and the mixture was heated on a steam bath for about one hour. To this mixture was added about 200 mL of water and the product was isolated by filtration and recrystallized from hexane to provide N-(1,1-dimethylethyl)-3-nitro-4-quinolinamine, m.p. 106°-108° C. Analysis: Calculated for C13H15 N3O2 : % C, 63.7; % H, 6.2; % N, 17.1; Found: % C, 64.0; % H, 6.3; % N, 17.1.

Workup

  1. temperatureheated at its
  2. temperaturereflux temperature for 30 minutes
  3. filtrationfiltered through celite
  4. washThe filtrate was washed repeatedly with 200 mL portions of cold sodium bicarbonate solution
  5. additionThe solution containing 4-chloro-3-nitroquinoline
  6. dry with materialwas dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. additionTo the solid was added
  10. additiona mixture of 20 g of tertiary-butylamine and 100 mL of N,N-dimethylformamide
  11. temperaturethe mixture was heated on a steam bath for about one hour
  12. additionTo this mixture was added about 200 mL of water
  13. customthe product was isolated by filtration
  14. customrecrystallized from hexane

Sources & evidence

ORD record
ord-856c46ec48ec49c794cf14b40e694508
Source dataset
uspto-grants-1998_05
Patent number
US05756747

Reaction notes

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