HCID 66704013, compound → HCID 66704005, compound

HRID 425263Notes

Reaction equation

HRID 425263 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([N:12]([C:15](=O)[CH3:16])[CH2:13][CH3:14])[CH:6]=[C:5]2[C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([N:12]([CH2:13][CH3:14])[CH2:15][CH3:16])[CH:6]=[C:5]2[C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1

Participants

3

Reactant 1

HCID 66704013HCID 66704013, compound

Product 1

HCID 66704005HCID 66704005, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

570 mg of 6-chloro-2-(N-acetyl-N-ethylamino)-4-(4-nitrophenyl)quinoline were suspended in 11.4 ml of THF and, under argon, added in portions to 3.1 ml of borane-THF complex. The temperature rose to 30° C. After stirring at room temperature for 3 hours, the solvent was removed by distillation and the residue was mixed with 50 ml of ethanol and 20 ml of concentrated HCl and heated on a water bath, cooled and distilled to remove the water. The residue was mixed with water, made alkaline with 2N NaOH, extracted with ethyl acetate and washed with water. The product was purified by MPLC chromatography using an MPRC cartridge with a mixture of 10 parts by volume of ethyl acetate, 5 parts by volume of n-heptane, 5 parts by volume of dichloromethane, 5 parts by volume of methanol and 1 part by volume of concentrated aqueous ammonia solution. A yellow solid product was isolated.

Workup

  1. additionadded in portions to 3.1 ml of borane-THF complex
  2. customrose to 30° C
  3. customthe solvent was removed by distillation
  4. additionthe residue was mixed with 50 ml of ethanol and 20 ml of concentrated HCl
  5. temperatureheated on a water bath
  6. temperaturecooled
  7. distillationdistilled
  8. customto remove the water
  9. additionThe residue was mixed with water
  10. extractionextracted with ethyl acetate
  11. washwashed with water
  12. customThe product was purified by MPLC chromatography
  13. additionwith a mixture of 10 parts by volume of ethyl acetate, 5 parts by volume of n-heptane, 5 parts by volume of dichloromethane, 5 parts by volume of methanol and 1 part by volume of concentrated aqueous ammonia solution
  14. customA yellow solid product was isolated

Sources & evidence

ORD record
ord-aa26f5b51bcb46889f5bc1d28b68e778
Source dataset
uspto-grants-2012_01
Patent number
US08106204B2

Reaction notes

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