Dichloromethane → HCID 21834412, compound

HRID 1740974Notes

Reaction equation

HRID 1740974 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][N:10]2C(=O)C3=CC=CC=C3C2=O)[N:5]=[C:4]([N:21]2[C:25]([CH3:26])=[CH:24][CH:23]=[C:22]2[CH3:27])[CH:3]=1.NN.ClCCl>CO>[NH2:10][CH2:9][CH2:8][C:6]1[N:5]=[C:4]([N:21]2[C:25]([CH3:26])=[CH:24][CH:23]=[C:22]2[CH3:27])[CH:3]=[C:2]([CH3:1])[CH:7]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 9321HydrazineHCID 21834442HCID 21834442, compound

Product 1

HCID 21834412HCID 21834412, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-methyl-2-(2,5-dimethylpyrrol-1-yl)-6-(2-phthalimidoethyl)pyridine (100 mg, 0.28 mmol) in 1.0 mL of methanol under nitrogen at room temperature was added hydrazine (0.018 mL, 0.56 mmol) via syringe. The mixture was stirred at room temperature overnight. Dichloromethane (2.0 mL) was added to the reaction. The precipitate was removed by filtration and washed with another 2 mL of dichloromethane. The combined filtrates were concentrated. The resulting residue was chromatographed on 7 g of silica gel, eluting with 100 mL of 5% methanol/dichloromethane followed by 200 mL of 96:4:1 dichloromethane/methanol/triethylamine to give 44 mg (68% yield) of 6-(2-aminoethyl)-4-methyl-2-(2,5-dimethylpyrrol-1-yl)pyridine as colorless syrup.

Workup

  1. customThe precipitate was removed by filtration
  2. washwashed with another 2 mL of dichloromethane
  3. concentrationThe combined filtrates were concentrated
  4. customThe resulting residue was chromatographed on 7 g of silica gel
  5. washeluting with 100 mL of 5% methanol/dichloromethane

Sources & evidence

ORD record
ord-4cd6121c542f4be28c55231ef761fd16
Source dataset
uspto-grants-1999_10
Patent number
US05972975

Reaction notes

Loading…