Sulfuric Acid → HCID 18187342, compound

HRID 1357647Notes

Reaction equation

HRID 1357647 reaction equation
[NH2:1][CH:2]1[C:7]([C:8](=[O:13])[C:9]([F:12])([F:11])[CH3:10])=[CH:6][CH:5]=[CH:4][N:3]1[C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1.S(=O)(=O)(O)O>CCOC(C)=O.CCCCCC>[Cl:20][C:17]1[CH:16]=[CH:15][C:14]2[NH:3][C:2]3[N:1]=[CH:4][CH:5]=[CH:6][C:7]=3[C:8]([OH:13])([C:9]([F:11])([F:12])[CH3:10])[C:19]=2[CH:18]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 18187290HCID 18187290, compound

Product 1

HCID 18187342HCID 18187342, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Method JJ: 2-Amino-N-(4-chlorophenyl)-3-(2,2-difluoropropionyl)pyridine (35) (190 mg, 0.640 mmol) was treated with conc. sulfuric acid (1 mL). The resulting red homogeneous solution was stirred at room temperature for 47.5 h. The reaction was quenched with saturated aqueous Na2CO3 (15 mL), and extracted with EtOAc (3×). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. Flash chromatography (50% EtOAc-hexane) provided 37 (173 mg, 91% yield) as an off-white solid (m.p. 188-190° C.).

Workup

  1. customThe reaction was quenched with saturated aqueous Na2CO3 (15 mL)
  2. extractionextracted with EtOAc (3×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-85f734a3de4c4f00adbd963d531a0db0
Source dataset
uspto-grants-2003_07
Patent number
US06593337B1

Reaction notes

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