Sulfuric Acid → HCID 22989705, compound

HRID 1168941Notes

Reaction equation

HRID 1168941 reaction equation
S(=O)(=O)(O)O.[CH:6]([O:9][C:10]1[CH:11]=[C:12](N)[CH:13]=[N:14][CH:15]=1)([CH3:8])[CH3:7].N([O-])=[O:18].[Na+].[OH-].[Na+].[Na+].[Cl-]>O>[CH:6]([O:9][C:10]1[CH:11]=[C:12]([OH:18])[CH:13]=[N:14][CH:15]=1)([CH3:8])[CH3:7]

Participants

7

Reactant 5

HCID 1118Sulfuric Acid2×HCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 10606940HCID 10606940, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 22989705HCID 22989705, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
2.5 °C

Procedure

A mixture of concentrated sulfuric acid (18 M, 2.64 mL), water (3.59 mL) and crushed ice (6.20 g) was added to 5-isopropoxy-3-pyridylamine (1.88 g, 12.38 mmol). The cold mixture (0-5° C.) was stirred for 10 min and a solution of sodium nitrite (0.85 g, 12.38 mmol) in water (2.5 mL) was then added. After stirring for 10 min, a boiling solution of concentrated sulfuric acid (8.0 mL) and water (6.2 mL) was added. The mixture was heated until all solids dissolved. Ice (5.0 g) was added to cool the solution. The pH was adjusted to 8 with 10% NaOH solution. Saturated NaCl solution (100 mL) was added, and the mixture was extracted with ethyl acetate (4×100 mL). The combined ethyl acetate extracts were dried (MgSO4), filtered and concentrated by rotary evaporation to give 1.69 g (89.4%) of a brown oil.

Workup

  1. stirringAfter stirring for 10 min
  2. temperatureThe mixture was heated until all solids
  3. dissolutiondissolved
  4. temperatureto cool the solution
  5. extractionthe mixture was extracted with ethyl acetate (4×100 mL)
  6. dry with materialThe combined ethyl acetate extracts were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-dafced9988e4407bb8e468087919aba4
Source dataset
uspto-grants-2003_09
Patent number
US06627648B1

Reaction notes

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