Water → Tert-butyl 2-(3-nitropyridin-4-yloxy)ethylcarbamate

HRID 69864Notes

Reaction equation

HRID 69864 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].[H-].[Na+].Cl[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][C:16]=1[N+:21]([O-:23])=[O:22].O>C1COCC1>[N+:21]([C:16]1[CH:17]=[N:18][CH:19]=[CH:20][C:15]=1[O:1][CH2:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:8])([CH3:10])[CH3:9])([O-:23])=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 2733206tert-butyl N-(2-hydroxyethyl)carbamateHCID 27357814-Chloro-3-nitropyridine

Product 1

HCID 69047653Tert-butyl 2-(3-nitropyridin-4-yloxy)ethylcarbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled solution (0° C.) of tert-butyl 2-hydroxyethylcarbamate (1.1 eq) in THF, NaH (1.3 eq) was added, stirred for 1 hr, and then 4-chloro-3-nitropyridine (1.0 eq) was added. The reaction mixture was stirred at RT overnight, poured into cold water, and extracted with EtOAc. Organic layer was dried over Na2CO3, filtered, and concentrated to yield tert-butyl 2-(3-nitropyridin-4-yloxy)ethylcarbamate. LCMS (m/z): 284.1 (MH+); LC Rt=2.09 min.

Workup

  1. stirringThe reaction mixture was stirred at RT overnight
  2. extractionextracted with EtOAc
  3. dry with materialOrganic layer was dried over Na2CO3
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-afb6c2f3f4194cc7956fbfdf80b47324
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Reaction notes

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