Sulfuric Acid → HCID 12183373, compound

HRID 2201017Notes

Reaction equation

HRID 2201017 reaction equation
[Cl:1][C:2]1[N: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][CH:3]=1.S(=O)(=O)(O)O.C(ON=O)(C)(C)C>C(O)(=O)C>[Cl:1][C:2]1[N:7]=[C:6]2[O:15][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[C:5]2=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 10906Tert-Butyl nitriteHCID 86663080HCID 86663080, compound

Product 1

HCID 12183373HCID 12183373, compoundYield 53.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

6-chloro-3-(2-methoxyphenyl)pyridin-2-amine (4.0 g, 17.04 mmol) was dissolved in glacial acetic acid (100 mL) and concentrated sulfuric acid (1 mL). A solution of t-butylnitrite (6.1 mL, 51.2 mmol) in 6 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 neutralized by saturated aq. NaHCO3 solution and the organic phase was separated from the aqueous phase. The aqueous phase extracted with methylene chloride and the combined organic layers was dried over sodium sulfate, concentrated and the residue was purified by silica column using hexanes and ethyl acetate as eluent to give 1.85 g of title compound.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutiondissolved in methylene chloride
  3. customthe organic phase was separated from the aqueous phase
  4. extractionThe aqueous phase extracted with methylene chloride
  5. dry with materialthe combined organic layers was dried over sodium sulfate
  6. concentrationconcentrated
  7. customthe residue was purified by silica column

Sources & evidence

ORD record
ord-a33d4303b4684d239af004e6cbeef11d
Source dataset
uspto-grants-2016_06
Patent number
US09359549B2

Reaction notes

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