Water → HCID 15068889, compound

HRID 2106728Notes

Reaction equation

HRID 2106728 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([OH:12])[CH:6]=[CH:5]2.C(=O)([O-])[O-].[Na+].[Na+].F[C:20]1[CH:21]=[N+:22]([O-:29])[CH:23]=[CH:24][C:25]=1[N+:26]([O-:28])=[O:27].O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([O:12][C:20]1[CH:21]=[N+:22]([O-:29])[CH:23]=[CH:24][C:25]=1[N+:26]([O-:28])=[O:27])[CH:6]=[CH:5]2

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 271446-Bromo-2-naphthalenolHCID 5940283-Fluoro-4-nitropyridin-1-ium-1-olate

Product 1

HCID 15068889HCID 15068889, compoundYield 227.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To 6-bromo-2-naphthol (8.43 g) in 80 ml DMF at room temperature was added sodium carbonate (8.0 g) portionwise, and after the addition was complete, the mixture was stirred for 10 minutes, and then a solution of 3-fluoro-4-nitropyridine-N-oxide (6.0 g) in 40 ml DMF was added dropwise. The reaction mixture was then stirred for six hours at room temperature. The mixture was then poured into water and extracted with ethyl acetate. The organic layer was washed with sat. NaCl solution and dried over Na2SO4. The filtrate was concentrated to yield a solid (31 g). This material was triturated with methanol to yield a solid, 10.0 g, m.p. 175°-177° C.

Workup

  1. additionafter the addition
  2. stirringThe reaction mixture was then stirred for six hours at room temperature
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with sat. NaCl solution
  5. dry with materialdried over Na2SO4
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-df1e72bfbc48485082466110045b0011
Source dataset
uspto-grants-1990_06
Patent number
US04931457

Reaction notes

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