HCID 12654468, compound → HCID 46189182, compound

HRID 1915023Notes

Reaction equation

HRID 1915023 reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[C:6]3[CH:16]=[CH:15][CH:14]=[CH:13][C:7]3=[CH:8][CH:9]=2)[N:4]=1)#[N:2].[H][H]>[Pd].C(O)(=O)C>[N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[C:7]3[CH:13]=[CH:14][CH:15]=[CH:16][C:6]3=2)[CH:11]=[CH:12][C:3]=1[CH2:1][NH2:2]

Participants

5

Reactant 2

HCID 12654468HCID 12654468, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 46189182HCID 46189182, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 2-cyanobenzo[h]quinoline (2.04 g, 10.0 mmol) and 10% palladium on carbon (0.40 g) in acetic acid (120 ml) was hydrogenated at ambient temperature, in a Parr reactor, with hydrogen gas at a pressure of 2 atm. After 4 hours, during which time absorbance of two hydrogen equivalents was observed, the reaction mixture was filtered and the solvent evaporated under reduced pressure. The oily residue was taken up with ethyl ether and the mixture washed with a 10% NaOH solution until an alkaline pH was achieved. The organic phase was then separated and dried over Na2SO4. The solvent was evaporated and the residue was purified by flash chromatography using MeOH as eluent. 1.87 g (90% yield) of 1-(benzo[h]quinolin-2-yl)methanamine in the form of a red solid was obtained.

Workup

  1. filtrationthe reaction mixture was filtered
  2. customthe solvent evaporated under reduced pressure
  3. washthe mixture washed with a 10% NaOH solution until an alkaline pH
  4. customThe organic phase was then separated
  5. dry with materialdried over Na2SO4
  6. customThe solvent was evaporated
  7. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-b57d727ee90543da8a143edcd7844e83
Source dataset
uspto-grants-2013_12
Patent number
US08614322B2

Reaction notes

Loading…