Acetic Acid → HCID 66823493, compound

HRID 591190Notes

Reaction equation

HRID 591190 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:12]([C:17]3[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=3)[C:20]#[N:21])[CH2:13][N+:14]([O-])=O)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(O)(=O)C>O1CCCC1.[Zn]>[NH2:14][CH2:13][CH:12]([C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[C:20]#[N:21])[C:8]1([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH2:11][CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 667475753-{1-[1-(4-Chlorophenyl)cyclobutyl]-2-nitroethyl}benzonitrile

Product 1

HCID 66823493HCID 66823493, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

3-{1-[1-(4-Chlorophenyl)cyclobutyl]-2-nitroethyl}benzonitrile (3.0 g, 8.8 mmol) was dissolved in tetrahydrofuran (37 ml) and zinc dust (8.63 g, 132 mmol) was added followed by acetic acid (7.34 ml, 8.8 mmol). The reaction mixture was stirred at room temperature for 2 h. The reaction mixture was filtered through celite and diluted with ethyl acetate. The solution was washed with aqueous sodium bicarbonate (two times), dried (magnesium sulfate) and concentrated in vacuo. Yield: 2.41 g (7.75 mmol, 88%)

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. additiondiluted with ethyl acetate
  3. washThe solution was washed with aqueous sodium bicarbonate (two times)
  4. dry with materialdried (magnesium sulfate)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bb398e1fa470456084bc3c5ac23a2c19
Source dataset
uspto-grants-2016_01
Patent number
US09238619B2

Reaction notes

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