HCID 59807049, compound → HCID 59807033, compound

HRID 1922376Notes

Reaction equation

HRID 1922376 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH2:14][CH:15]([N:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1)[CH3:16])[C:9](=[O:22])[CH2:8][CH2:7]2)([O-])=O.[H][H]>[Pd].C(O)C>[NH2:1][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH2:14][CH:15]([N:17]1[CH2:18][CH2:19][CH2:20][CH2:21]1)[CH3:16])[C:9](=[O:22])[CH2:8][CH2:7]2

Participants

5

Reactant 2

HCID 59807049HCID 59807049, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59807033HCID 59807033, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 6-nitro-1-(2-(pyrrolidin-1-yl)propyl)-3,4-dihydroquinolin-2(1H)-one (585 mg, 1.93 mmol) and palladium on activated carbon (10%, 103 mg, 0.096 mmol) in 15 mL ethanol was stirred under a balloon of hydrogen overnight. The suspension was filtered through a pad of silica gel. The filter pad was rinsed with 20 mL of 2M NH3 in methanol and the filtrate was concentrated to give a viscous oil. The crude product was used without further purification. (490 mg, 92.9%). 1H-NMR (CDCl3) δ: 7.20 (d, J=8.7 Hz, 1H), 6.63 (dd, J=2.4, 8.7 Hz, 1H), 6.51 (d, J=2.4 Hz, 1H), 4.37 (d, J=7.2 Hz, 2H), 3.58 (brs, 2H), 2.82-2.77 (m, 2H), 2.63-2.58 (m, 2H), 2.1 (br s, 4H), 1.80-1.62 (br s, 5H), 1.30 (d, J=6.6 Hz, 3H).

Workup

  1. filtrationThe suspension was filtered through a pad of silica gel
  2. washThe filter pad was rinsed with 20 mL of 2M NH3 in methanol
  3. concentrationthe filtrate was concentrated
  4. customto give a viscous oil
  5. customThe crude product was used without further purification

Sources & evidence

ORD record
ord-7438b577714b4f959da99603d5e471d5
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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