Trifluoroacetic acid → 3-(5-Amino-5,6,7,8-tetrahydro-naphthalen-2-yl)-acrylonitrile

HRID 32099Notes

Reaction equation

HRID 32099 reaction equation
C(OC(=O)[NH:7][CH:8]1[C:17]2[C:12](=[CH:13][C:14]([CH:18]=[CH:19][C:20]#[N:21])=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][CH:8]1[CH2:9][CH2:10][CH2:11][C:12]2[CH:13]=[C:14]([CH:18]=[CH:19][C:20]#[N:21])[CH:15]=[CH:16][C:17]1=2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68925513HCID 68925513, compound

Product 1

HCID 689266503-(5-Amino-5,6,7,8-tetrahydro-naphthalen-2-yl)-acrylonitrileYield 89.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [6-(2-cyano-vinyl)-1,2,3,4-tetrahydro-naphthalen-1-yl]-carbamic acid tert-butyl ester (2.7 g, 9.05 mmol) in DCM (40 mL) was added TFA (15 mL). The resulting mixture was stirred at RT for 1 h. Solvent was removed. The residue was redissolved in EtOAc. The organic layer was washed with sat. NaHCO3, H2O, brine, dried over MgSO4 and removed solvent. The crude product was purified by chromatography on silica gel. Elution with CH2Cl2:MeOH (2M NH3) mixture (97:3) gave final compound (1.6 g, 89%). MS m/z: 199.3 (M+H). Calc'd. for C13H14N2-198.26.

Workup

  1. customSolvent was removed
  2. dissolutionThe residue was redissolved in EtOAc
  3. washThe organic layer was washed with sat. NaHCO3, H2O, brine
  4. dry with materialdried over MgSO4
  5. customremoved solvent
  6. customThe crude product was purified by chromatography on silica gel
  7. washElution with CH2Cl2

Sources & evidence

ORD record
ord-74fb4b3169ef468f8151be64dc6fb1d7
Source dataset
uspto-grants-2008_09
Patent number
US07425631B2

Reaction notes

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