Butylamine → HCID 9901307, compound

HRID 1006152Notes

Reaction equation

HRID 1006152 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][OH:13])=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:14])[CH:3]=1.[CH2:15]([NH2:19])[CH2:16][CH2:17][CH3:18]>N1CCCC1>[CH2:15]([NH:19][C:12]([C:8]1[CH:7]=[C:6]2[C:11]([C:2]([N:19]3[CH2:18][CH2:17][CH2:16][CH2:15]3)=[CH:3][C:4]([CH3:14])=[N:5]2)=[CH:10][CH:9]=1)=[O:13])[CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 8007ButylamineHCID 11264243HCID 11264243, compound

Product 1

HCID 9901307HCID 9901307, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 31268PyrrolidineSolvent

Procedure

(4-Chloro-2-methyl-quinolin-7-yl)-methanol (example 2, 200 mg, 0.80 mmol) was refluxed in butylamine (2 mL) for 6 h. After cooling the reaction mixture was partitioned between sat. aq. ammonium chloride solution and dichloromethane. The organic layer was separated, dried (MgSO4), and evaporated. The residue was chromatographed (SiO2, CH2Cl2/MeOH 19:1) to produce a yellow oil, which was heated in pyrrolidine (2 mL) at 70° C. for 16 h. After cooling the reaction mixture was partitioned between sat. aq. ammonium chloride solution and dichloromethane. The organic layer was separated, dried (MgSO4), and evaporated. Chromatography (SiO2, dichloromethane/methanol 19:1) afforded the title compound (108 mg, 43%). White solid, ISP-MS: m/e=312.3 ([M+H]+).

Workup

  1. temperatureAfter cooling the reaction mixture
  2. customwas partitioned between sat. aq. ammonium chloride solution and dichloromethane
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue was chromatographed (SiO2, CH2Cl2/MeOH 19:1)
  7. customto produce a yellow oil, which
  8. temperatureAfter cooling the reaction mixture
  9. customwas partitioned between sat. aq. ammonium chloride solution and dichloromethane
  10. customThe organic layer was separated
  11. dry with materialdried (MgSO4)
  12. customevaporated

Sources & evidence

ORD record
ord-a1cf053fa2144749a76ed1f0e388fe7a
Source dataset
uspto-grants-2004_09
Patent number
US06787558B2

Reaction notes

Loading…