Ethyl Acetate → HCID 66745877, compound

HRID 1467035Notes

Reaction equation

HRID 1467035 reaction equation
[CH:1]1([O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-])=O)[C:9]=2[C:10]#[N:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CCOC(C)=O>C1COCC1.CC(O)=O.[Fe]>[NH2:16][C:12]1[CH:13]=[CH:14][CH:15]=[C:8]([O:7][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[C:9]=1[C:10]#[N:11]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 66747182HCID 66747182, compound

Product 1

HCID 66745877HCID 66745877, compoundYield 104%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 23444217Acetic acid tetrahydrofuranSolvent

Procedure

To a solution of 2-(cyclohexyloxy)-6-nitrobenzonitrile (Example 36c, 50.0 g, 0.20 mol) in THF/AcOH (1:1 by volume, 500 mL) was added iron powder (34.0 g, 0.61 mol) in one portion at room temperature under nitrogen. The reaction mixture was refluxed for 40 min under nitrogen and cooled down to room temperature and EtOAc (2 L) was added. The precipitate that formed was filtered off and washed with EtOAc. The organic layer was separated and washed successively with water (2×300 mL), aqueous NaOH (1.0 N, 2×300 mL), saturated Na2CO3 solution (300 mL), brine (300 mL), dried over Na2SO4 filtered and evaporated under reduced pressure. The residue was purified by chromatography on silica gel eluting with 25% EtOAc in hexanes to give 2-amino-6-(cyclohexyloxy)benzonitrile as a pale yellow oil (45.0 g, 94%), which solidified after storage overnight at room temperature.

Workup

  1. temperatureThe reaction mixture was refluxed for 40 min under nitrogen
  2. customThe precipitate that formed
  3. filtrationwas filtered off
  4. washwashed with EtOAc
  5. customThe organic layer was separated
  6. washwashed successively with water (2×300 mL), aqueous NaOH (1.0 N, 2×300 mL), saturated Na2CO3 solution (300 mL), brine (300 mL)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. customThe residue was purified by chromatography on silica gel eluting with 25% EtOAc in hexanes

Sources & evidence

ORD record
ord-e589651729df4d84887e5d54e2da70f1
Source dataset
uspto-grants-2015_04
Patent number
US09000054B2

Reaction notes

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