Stannous chloride dihydrate → HCID 58851268, compound

HRID 1696533Notes

Reaction equation

HRID 1696533 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH:6]=[CH:5]2.[N:13]([O-])=O.[Na+].O.O.Cl[Sn]Cl.[CH:22]1([C:27](=O)[CH2:28][C:29]#[N:30])[CH2:26][CH2:25][CH2:24][CH2:23]1>Cl.O>[NH2:30][C:29]1[N:1]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[NH:8][C:7](=[O:12])[CH:6]=[CH:5]3)[N:13]=[C:27]([CH:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)[CH:28]=1

Participants

8

Reactant 4

HCID 61436Stannous chloride dihydrateHCID 128107976-Aminoquinolin-2-olHCID 135921183-Cyclopentyl-3-oxopropanenitrileHCID 23668193Sodium Nitrite

Product 1

HCID 58851268HCID 58851268, compoundYield 57%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 6-aminoquinolin-2(1H)-one (0.72 g, 4.5 mmol, see Example A41) in conc. HCl (5 mL) was slowly added NaNO2 (0.43 g, 6.3 mmol) solution in H2O (5 mL) at 0° C. After stirring for 1 h, SnCl2.2H2O (2.0 g, 9.0 mmol), dissolved in conc. HCl (7 mL), was slowly added at such a rate that the temperature of the mixture did not rise above 5° C., After stirring for 2 h, the resultant solid was filtered, dried, and suspended in EtOH. To this were added 3-cyclopentyl-3-oxopropanenitrile (0.68 g, 4.9 mmol) and a few drops of HCl and the mixture was heated at 80° C. for 16 h. The solution was concentrated, dissolved in satd. NaHCO3 solution and the product was extracted with EtOAc (2×30 mL). The combined organic extracts were washed with brine, dried (Na2SO4), concentrated and the resultant solid triturated with toluene (10 mL) and filtered to yield 6-(5-amino-3-cyclopentyl-1H-pyrazol-1-yl)quinolin-2(1H)-one (0.75 g, 57% yield) as a solid. 1H NMR (400 MHz, DMSO-d6): δ 7.95 (d, J=10.0 Hz, 1H), 7.81 (d, J=2.4 Hz, 1H), 7.68 (dd, J=8.8 Hz, 2.0 Hz, 1H), 7.35 (d, J=8.8 Hz, 1H), 6.54 (d, J=8.8 Hz, 1H), 5.32 (s, 1H), 5.24 (brs, 2H), 2.92-2.84 (m, 1H), 1.94-1.86 (m, 2H), 1.73-1.57 (m, 6H); MS (ESI) m/z: 295.2 (M+H+).

Workup

  1. customat 0° C
  2. additionwas slowly added at such a rate that the temperature of the mixture
  3. customdid not rise above 5° C.
  4. stirringAfter stirring for 2 h
  5. filtrationthe resultant solid was filtered
  6. customdried
  7. concentrationThe solution was concentrated
  8. dissolutiondissolved in satd
  9. extractionNaHCO3 solution and the product was extracted with EtOAc (2×30 mL)
  10. washThe combined organic extracts were washed with brine
  11. dry with materialdried (Na2SO4)
  12. concentrationconcentrated
  13. customthe resultant solid triturated with toluene (10 mL)
  14. filtrationfiltered

Sources & evidence

ORD record
ord-3c7dd275421d4149ada1b2707d4c1ffd
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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