Water → 1-Benzyl-4-benzyloxy-3-nitro-pyridin-2-one

HRID 2214447Notes

Reaction equation

HRID 2214447 reaction equation
[OH:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([OH:11])[CH:5]=[CH:4][N:3]=1.[H-].[Na+].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>CN(C)C=O>[CH2:14]([N:3]1[CH:4]=[CH:5][C:6]([O:11][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:7]([N+:8]([O-:10])=[O:9])[C:2]1=[O:1])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 178526878HCID 178526878, compound

Product 1

HCID 219476521-Benzyl-4-benzyloxy-3-nitro-pyridin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4.68 g (30 mmol) of 2,4-dihydroxy-3-nitro-pyridine in 100 ml of dimethylformamide was combined batchwise at ambient temperature with 2.88 g (60 mmol) of a 50% suspension of sodium hydride in paraffin oil and stirred for 15 minutes. Then 8.91 ml (75 mmol) of benzylbromide were added and the mixture was stirred for 24 hours at 80° C. The solution was then carefully stirred into approx. 250 ml of water and extracted three times with 70 ml of ethyl acetate. The extracts were washed with saturated sodium chloride solution, dried and evaporated down in vacuo. The residue was triturated with diethyl ether, suction filtered and dried. The product thus obtained was further processed without any purification.

Workup

  1. stirringthe mixture was stirred for 24 hours at 80° C
  2. extractionextracted three times with 70 ml of ethyl acetate
  3. washThe extracts were washed with saturated sodium chloride solution
  4. customdried
  5. customevaporated down in vacuo
  6. customThe residue was triturated with diethyl ether, suction
  7. filtrationfiltered
  8. customdried
  9. customThe product thus obtained
  10. customwas further processed without any purification

Sources & evidence

ORD record
ord-0af2724e20044dd08534a17865f69187
Source dataset
uspto-grants-2006_09
Patent number
US07109192B2

Reaction notes

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