Sulfuric Acid → HCID 86663079, compound

HRID 2201014Notes

Reaction equation

HRID 2201014 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](N)[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15]C)=[CH:4][N:3]=1.S(=O)(=O)(O)O.C(ON=O)(C)(C)C>C(O)(=O)C>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[O:15][C:6]=2[CH:7]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 10906Tert-Butyl nitriteHCID 86663078HCID 86663078, compound

Product 1

HCID 86663079HCID 86663079, compoundYield 76.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

2-chloro-5-(2-methoxyphenyl)pyridin-4-amine (7.5 g, 31.96 mmol) was dissolved in glacial acetic acid (200 mL) and concentrated sulfuric acid (1 mL). A solution of t-butylnitrite (11.39 mL, 95.87 mmol) in 10 mL of acetic acid was added drop wise and stirred for 30 minutes. The reaction mixture was concentrated under reduced pressure, dissolved in methylene chloride. The reaction mixture was dried over sodium sulfate, concentrated and the residue was purified by silica column using hexanes and ethyl acetate as eluent to give 5.0 g of title compound.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutiondissolved in methylene chloride
  3. dry with materialThe reaction mixture was dried over sodium sulfate
  4. concentrationconcentrated
  5. customthe residue was purified by silica column

Sources & evidence

ORD record
ord-a07b86c049ee4927be9de9f79ad84b10
Source dataset
uspto-grants-2016_06
Patent number
US09359549B2

Reaction notes

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