Sulfuric Acid → ethyl 1-aminospiro[4H-naphthalene-3,1'-cyclohexane]-2-carboxylate

HRID 1886899Notes

Reaction equation

HRID 1886899 reaction equation
OS(O)(=O)=O.[CH2:6]([C:13]1([CH:19]([C:25]#[N:26])[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>CCOCC>[NH2:26][C:25]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][C:13]2([CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[C:19]=1[C:20]([O:22][CH2:23][CH3:24])=[O:21]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 14435569Ethyl 2-(1-benzylcyclohexyl)-2-cyanoacetate

Product 1

HCID 793326ethyl 1-aminospiro[4H-naphthalene-3,1'-cyclohexane]-2-carboxylate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Concentrated H2SO4 (4.59 ml) was added dropwise to ethyl 2-(1-benzylcyclohexyl)-2-cyanoacetate (2.46 g, 8.62 mmol) at 0° C. The mixture was stirred at room temperature for 7 h. Ice water was added to the mixture resulting in a precipitate. The precipitate was taken up in Et2O and washed with 28% NH3 solution. The organics were washed with water, dried over Na2SO4, filtered, and concentrated to an orange oil.

Workup

  1. customresulting in a precipitate
  2. washwashed with 28% NH3 solution
  3. washThe organics were washed with water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to an orange oil

Sources & evidence

ORD record
ord-9c6ce4ff567d41328f64de37ff218a4e
Source dataset
uspto-grants-2013_08
Patent number
US08501722B2

Reaction notes

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