Methanol → HCID 55023121, compound

HRID 340429Notes

Reaction equation

HRID 340429 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:8][CH2:7][CH2:6][CH2:5]1.CO.Cl[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][N:13]=1.O>C(OCC)(=O)C>[N+:18]([C:15]1[CH:16]=[CH:17][C:12]([NH:1][CH2:2][CH2:3][N:4]2[CH2:8][CH2:7][CH2:6][CH2:5]2)=[N:13][CH:14]=1)([O-:20])=[O:19]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 13441-Pyrrolidineethanamine2×HCID 783082-Chloro-5-nitropyridine

Product 1

HCID 55023121HCID 55023121, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1-(2-aminoethyl)pyrrolidine (237 μl) was added to a methanol (1 ml) suspension containing 2-chloro-5-nitropyridine (100 mg), followed by stirring at room temperature for 3 hours and 30 minutes. 1-(2-aminoethyl)pyrrolidine (158 μl) was added, followed by stirring for 2 hours. Water and ethyl acetate were added to the reaction mixture. The organic layer was collected, washed with 10% saline and then with saturated saline, and dried over anhydrous magnesium sulfate, and the solvent was distilled away under reduced pressure. Diisopropylether was added to the obtained residue, solid matter was collected by filtration and washed with diisopropylether and hexane, and a yellow solid of 5-nitro-N-(2-(pyrrolidin-1-yl)ethyl)pyridin-2-amine (27 mg) was thus obtained.

Workup

  1. stirringby stirring for 2 hours
  2. customThe organic layer was collected
  3. washwashed with 10% saline
  4. dry with materialwith saturated saline, and dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled away under reduced pressure
  6. additionDiisopropylether was added to the obtained residue, solid matter
  7. filtrationwas collected by filtration
  8. washwashed with diisopropylether and hexane

Sources & evidence

ORD record
ord-a7c110ea709943359ecfedbe4d2a0e2a
Source dataset
uspto-grants-2014_11
Patent number
US08895585B2

Reaction notes

Loading…