Water → 8-Chlorobenzofuro[3,2-c]pyridine

HRID 634548Notes

Reaction equation

HRID 634548 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:15]C)=[C:6]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][C:13]=2N)[CH:7]=1.C1COCC1.O>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:15][C:13]3[CH:12]=[CH:11][N:10]=[CH:9][C:8]=3[C:6]=2[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8028TetrahydrofuranHCID 509670043-(5-Chloro-2-methoxyphenyl)pyridin-4-amine

Product 1

HCID 441784398-Chlorobenzofuro[3,2-c]pyridine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3-(5-chloro-2-methoxyphenyl)pyridin-4-amine (2 g, 8.5 mmol) was dissolved in 25 mL of acetic acid and 10 mL of THF at −10° C. To the solution t-butyl nitrile (2 ml, 17 mmol) was dropwisely added. The mixture was warmed to room temperature overnight. Water was added to the reaction mixture and was extracted by dichloromethane, the organic layer was then dried by MgSO4 and concentrated. The residue was then purified by column chromatography using THF:hexane (1:3, v/v) as the eluent. 0.8 g (46%) of product was collected as the product.

Workup

  1. customat −10° C
  2. extractionwas extracted by dichloromethane
  3. dry with materialthe organic layer was then dried by MgSO4
  4. concentrationconcentrated
  5. customThe residue was then purified by column chromatography
  6. custom0.8 g (46%) of product was collected as the product

Sources & evidence

ORD record
ord-3a7dde98dbdd4dc79319995cc86ee9a1
Source dataset
uspto-grants-2016_04
Patent number
US09324949B2

Reaction notes

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