2-Chloro-5-nitropyridine → HCID 32810000, compound

HRID 2273091Notes

Reaction equation

HRID 2273091 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 641498(R)-3-Methylmorpholine

Product 1

HCID 32810000HCID 32810000, compoundYield 77.6%

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 (R)-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 1.07 g of (R)-3-methyl-4-(5-nitro-pyridin-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-bd9c0c1e54034023b0aec4d65ff649d2
Source dataset
uspto-grants-2015_09
Patent number
US09120812B2

Reaction notes

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