2-Chloro-5-nitropyridine → HCID 32810003, compound

HRID 2273089Notes

Reaction equation

HRID 2273089 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[CH3:11][C@H:12]1[CH2:17][O:16][CH2:15][CH2:14][NH:13]1>CO>[CH3:11][C@H:12]1[CH2:17][O:16][CH2:15][CH2:14][N:13]1[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 783082-Chloro-5-nitropyridineHCID 12012220(3S)-3-methylmorpholine

Product 1

HCID 32810003HCID 32810003, compoundYield 97.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 1 g (6.18 mmol) of 2-chloro-5-nitropyridine and 1.31 g (12.36 mmol) of (S)-3-methylmorpholine is heated in a Biotage microwave machine for 1 hour at 150° C. The reaction medium is taken up in MeOH and then evaporated under reduced pressure. The residue is chromatographed on silica gel, eluting with a DCM/MeOH mixture from (100/0 v/v) up to (95/5 v/v) to give 1.35 g of (S)-3-methyl-4-(5-nitropyridin-2-yl)morpholine.

Workup

  1. customevaporated under reduced pressure
  2. customThe residue is chromatographed on silica gel
  3. washeluting with a DCM/MeOH mixture from (100/0 v/v) up to (95/5 v/v)

Sources & evidence

ORD record
ord-ab2bfdf1c49844308cc179a4b70d0db0
Source dataset
uspto-grants-2015_09
Patent number
US09120812B2

Reaction notes

Loading…