Ethyl bromoacetate → 4-Chloro-1-ethyloxycarbonylmethyl-3-nitro-2-pyridinone

HRID 1953462Notes

Reaction equation

HRID 1953462 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([OH:10])[C:5]=1[N+:11]([O-:13])=[O:12].Br[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]>C1COCC1>[Cl:3][C:4]1[CH:9]=[CH:8][N:7]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:6](=[O:10])[C:5]=1[N+:11]([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 178526742HCID 178526742, compound

Product 1

HCID 232982444-Chloro-1-ethyloxycarbonylmethyl-3-nitro-2-pyridinone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Sodium hydride (60% dispersion in mineral oil, 7.5 g, 0.188 mol) was added to a stirred solution of 4-chloro-2-hydroxy-3-nitropyridine (23.68 g, 0.126 mol) in THF (250 mL) at 0° C. After 25 min ethyl bromoacetate (16.7 mL, 0.151 mol) was added and the reaction was warmed to 60° C. After 20 h the reaction was cooled and washed with brine acidified with 1M HCl. The organic layer was dried (Na2SO4) and evaporated in vacuo to a solid which was recrystallised from ethyl acetate/hexanes to give the title compound;

Workup

  1. temperatureAfter 20 h the reaction was cooled
  2. washwashed with brine
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. customevaporated in vacuo to a solid which
  5. customwas recrystallised from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-03d0517373e941e296b135920114cc7f
Source dataset
uspto-grants-2000_09
Patent number
US06117888

Reaction notes

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