HCID 59754301, compound → 2-Quinolinecarbonitrile,6-amino-(9CI)

HRID 501575Notes

Reaction equation

HRID 501575 reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:13]([O-])=O)[CH:9]=2)[N:4]=1)#[N:2]>CCOC(C)=O.CO.[H][H].[Pd]>[C:1]([C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH2:13])[CH:9]=2)[N:4]=1)#[N:2]

Participants

6

Reactant 1

HCID 59754301HCID 59754301, compound

Product 1

HCID 451170492-Quinolinecarbonitrile,6-amino-(9CI)Yield 79%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

Compound 45B (212 mg, 1.1 mmol) was dissolved in 30 mL of a 1:2 mixture of EtOAc and MeOH and hydrogenated at 1 atmosphere of hydrogen in the presence of 10% Pd/C (42 mg, 20 wt. %) for 1 h. The reaction was filtered, concentrated and purified by silica gel flash chromatography eluting with 2-3% MeOH—CH2Cl2 to give the title compound (142 mg, 79%) as a light yellow solid. LC/MS m/z 170 [M+H]+.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated
  3. custompurified by silica gel flash chromatography
  4. washeluting with 2-3% MeOH—CH2Cl2

Sources & evidence

ORD record
ord-3edae6e6028a40e29b7a528f74f8a15c
Source dataset
uspto-grants-2010_08
Patent number
US07772267B2

Reaction notes

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