Sodium Hydroxide → HCID 178429283, compound

HRID 1993630Notes

Reaction equation

HRID 1993630 reaction equation
[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4](N)[CH:3]=1.N([O-])=[O:13].[Na+].[OH-].[Na+]>S(=O)(=O)(O)O.O>[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]([OH:13])[CH:3]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 2431652-Amino-4-methyl-5-nitropyridineHCID 23668193Sodium Nitrite

Product 1

HCID 178429283HCID 178429283, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve 4-methyl-5-nitro-pyridin-2-ylamine (3.0 mmol, 0.5 g) in 0.5 mL of sulfuric acid. Add 7.6 mL of water and cool the solution down to 0° C. Add sodium nitrite (4.5 mmol, 0.3 g) and stir the mixture for two hours, allowing to reach room temperature. Dilute with water and add aq. sodium hydroxide solution 10% until basic pH. Extract in ethyl acetate and wash combined organic layers with saturated aq. sodium chloride solution. Dry over sodium sulfate, filter, and concentrate under reduced pressure to give 4-methyl-5-nitro-pyridin-2-ol. MS(ES): m/z=155 [M+H].

Workup

  1. customto reach room temperature
  2. extractionExtract in ethyl acetate
  3. washwash
  4. dry with materialDry over sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-176a861e9ad14a2b9a1e0098b91a3add
Source dataset
uspto-grants-2010_01
Patent number
US07652015B2

Reaction notes

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