Hydrochloric Acid → 6-((4-Oxocyclohexyl)oxy)nicotinonitrile

HRID 459914

Reaction equation

HRID 459914 reaction equation
Cl.CC1(C)CO[C:6]2([CH2:13][CH2:12][CH:11]([O:14][C:15]3[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][N:16]=3)[CH2:10][CH2:9]2)[O:5]C1>CC(C)=O>[O:5]=[C:6]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][N:16]=2)[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 184453076-(3,3-Dimethyl-1,5-dioxa-spiro[5.5]undec-9-yloxy)-nicotinonitrile

Product 1

HCID 184453106-((4-Oxocyclohexyl)oxy)nicotinonitrileYield 71%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Combine hydrochloric acid (1.0M aq., 20 mL) with a solution of 6-(3,3-dimethyl-1,5-dioxa-spiro[5.5]undec-9-yloxy)-nicotinonitrile (2000 mg, 6.61 mmol) in acetone (25 mL). Stir at room temperature for 2 h then at 40–50° C. for 1 h. Concentrate the reaction mixture. Partition the residue between EtOAc/hex (25 mL) and K2CO3 (aq. sat. 20 mL). Wash the organic layer with water, brine, and dry it over sodium sulfate, filter and concentrate. Triturate the residue with EtOAc/hexanes (1/4) to provide a white solid which is further purified by flash chromatography (EtOAc/Hexanes 1/4) to give 1010 mg (71% yield) as a white solid.

Workup

  1. waitat 40–50° C. for 1 h
  2. concentrationConcentrate the reaction mixture
  3. customPartition the residue between EtOAc/hex (25 mL) and K2CO3 (aq. sat. 20 mL)
  4. washWash the organic layer with water, brine
  5. dry with materialdry it over sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate
  8. customTriturate the residue with EtOAc/hexanes (1/4)
  9. customto provide a white solid which
  10. customis further purified by flash chromatography (EtOAc/Hexanes 1/4)
  11. customto give 1010 mg (71% yield) as a white solid

Sources & evidence

ORD record
ord-a5add9904f4a4db6b932dcaeb14eeb49
Source dataset
uspto-grants-2007_03
Patent number
US07196100B2

Linked notes

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