1-Naphthol → 2-[(Naphthalen-1-yl)oxy]-5-nitropyridine

HRID 1247905Notes

Reaction equation

HRID 1247905 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:17]1([OH:27])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1.[O-][Si]([O-])=O.[Mg+2]>CN(C=O)C.CCCCCC.C(OCC)(=O)C>[C:17]1([O:27][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=2)[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1

Participants

8

Reactant 4

HCID 70051-NaphtholHCID 11430Potassium Carbonate2×HCID 61680MAGNESIUM SILICATE (synthetic)2×HCID 783082-Chloro-5-nitropyridine

Product 1

HCID 134724102-[(Naphthalen-1-yl)oxy]-5-nitropyridine

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
125 °C

Procedure

To a solution of 17.0 g. (0.107 mol.) of 2-chloro-5-nitro pyridine in 250 ml of DMF was added 15.4 g. (0.112 mol.) of potassium carbonate and 15.5 g. (0.107 mol.) of 1-naphthol. The resulting mixture was heated up to 125° C. for 3 hours. Additional potassium carbonate (1.5 g., 0.011 mol.) was added. This mixture was continued heating for 7 hours, cooled, and concentrated to give a black gummy product. It was then dissolved in 200 ml. of ethyl acetate. Florisil (60-100 mesh, 40 g.) was added to the above solution and the resulting mixture was concentrated to give brown powder. This material was packed on top of a column (450 g. florisil in hexane). Elution with hexane/ethyl acetate (96:4) gave 14.3 g. (0.054 mol., 50.3% of bright yellow crystals; mp. 87.3°-89.3° C.

Workup

  1. temperatureThis mixture was continued heating for 7 hours
  2. temperaturecooled
  3. concentrationconcentrated
  4. customto give a black gummy product
  5. dissolutionIt was then dissolved in 200 ml
  6. concentrationthe resulting mixture was concentrated
  7. customto give brown powder
  8. washElution with hexane/ethyl acetate (96:4)
  9. customgave 14.3 g

Sources & evidence

ORD record
ord-b69db058cf0344ab8475dddbfc614502
Source dataset
uspto-grants-1985_06
Patent number
US04521426

Reaction notes

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