Water → 4-Nitro-3-(5,6,7,8-tetrahydro-1-naphthyloxy)pyridine-N-oxide

HRID 2106726Notes

Reaction equation

HRID 2106726 reaction equation
[C:1]1([OH:11])[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[Na+].[Na+].F[C:19]1[CH:20]=[N+:21]([O-:28])[CH:22]=[CH:23][C:24]=1[N+:25]([O-:27])=[O:26].O>CN(C=O)C>[N+:25]([C:24]1[CH:23]=[CH:22][N+:21]([O-:28])=[CH:20][C:19]=1[O:11][C:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1)([O-:27])=[O:26]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 682585,6,7,8-Tetrahydro-1-naphtholHCID 5940283-Fluoro-4-nitropyridin-1-ium-1-olate

Product 1

HCID 150688874-Nitro-3-(5,6,7,8-tetrahydro-1-naphthyloxy)pyridine-N-oxide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To 5,6,7,8-tetrahydro-1-naphthol (6.0 g) in DMF (100 ml) was added Na2CO3 (10 g) portionwise at room temperature. Then a solution of 3-fluoro-4-nitropyridine-N-oxide (6.0 g) in 20 ml of DMF was added dropwise and the mixture was stirred at room temperature for four hours. The mixture was then poured into water and extracted with ethyl acetate. The organic layer was washed with water and dried (sat NaCl, anhy. MgSO4).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. customdried (

Sources & evidence

ORD record
ord-d88116a2cd204992a095744afb38592c
Source dataset
uspto-grants-1990_06
Patent number
US04931457

Reaction notes

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