Hydrochloric Acid → HCID 66704006, compound

HRID 425261Notes

Reaction equation

HRID 425261 reaction equation
[C:1]([NH:4][C:5]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Cl:24])[CH:11]=2)[N:6]=1)(=O)[CH3:2].C(O)C.Cl>C1COCC1>[Cl:24][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[N:6]=[C:5]([NH:4][CH2:1][CH3:2])[CH:14]=[C:13]2[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 66703994HCID 66703994, compound2×

Product 1

HCID 66704006HCID 66704006, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

500 mg of 2-acetylamino-6-chloro-4-(4-nitrophenyl)quinoline (compound 1c) were suspended in 10 ml of THF and, under argon, added in portions to 2.9 ml of borane-THF complex. Foaming was followed by formation of a yellow solution. After stirring at room temperature for 12 hours, the solution was mixed with 5 ml of ethanol and 2 ml of concentrated HCl and heated on a water bath, cooled and distilled to remove 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 1 part by volume of ethyl acetate, 2 parts by volume of toluene. A yellow solid product was isolated.

Workup

  1. additionadded in portions to 2.9 ml of borane-THF complex
  2. temperatureheated on a water bath
  3. temperaturecooled
  4. distillationdistilled
  5. customto remove water
  6. additionThe residue was mixed with water
  7. extractionextracted with ethyl acetate
  8. washwashed with water
  9. customThe product was purified by MPLC chromatography
  10. additionwith a mixture of 1 part by volume of ethyl acetate, 2 parts by volume of toluene
  11. customA yellow solid product was isolated

Sources & evidence

ORD record
ord-7e43a73e898845f8b2b4be15f2975adc
Source dataset
uspto-grants-2012_01
Patent number
US08106204B2

Reaction notes

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