Ethyl Acetate → HCID 9835084, compound

HRID 1372536Notes

Reaction equation

HRID 1372536 reaction equation
[NH2:1][C:2]1[C:14](Br)=[C:13]2[C:5]([C:6]3[C:11]([CH2:16][CH3:17])([CH2:12]2)[CH2:10][CH2:9][C:8](=[O:18])[C:7]=3[CH3:19])=[CH:4][CH:3]=1.[C:20]([Cu])#[N:21].CN1CCCC1=O.CCOC(C)=O>O>[NH2:1][C:2]1[C:14]([C:20]#[N:21])=[C:13]2[C:5]([C:6]3[C:11]([CH2:16][CH3:17])([CH2:12]2)[CH2:10][CH2:9][C:8](=[O:18])[C:7]=3[CH3:19])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 13387N-methyl-2-pyrrolidoneHCID 9966834HCID 9966834, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 9835084HCID 9835084, compoundYield 59.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of crude 7-amino-8-bromo-9a-ethyl-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (0.97 g, 3.02 mmol), CuCN (0.318 g, 3.55 mmol), and 1-methyl-2-pyrrolidinone (NMP, 6 mL) was placed under a N2 atmosphere, stirred, and heated in an oil bath at 160–170° C. for 5.5 hours. After cooling to room temperature, the mixture was added to EtOAc (200 mL) and water (200 mL) and filtered through a pad of solka-floc. The organic portion of the filtrate was washed with water (5×200 mL) and brine (100 mL), dried over MgSO4, filtered, and evaporated under vacuum to a red oil (0.8 g). The crude product was purified by chromatography on EM silica gel 60 (2.75×25 cm column), eluting with 5% EtOAc in CH2Cl2, to afford 7-amino-8-cyano-9a-ethyl-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (0.48 g) as a solid.

Workup

  1. temperatureheated in an oil bath at 160–170° C. for 5.5 hours
  2. filtrationfiltered through a pad of solka-floc
  3. washThe organic portion of the filtrate was washed with water (5×200 mL) and brine (100 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated under vacuum to a red oil (0.8 g)
  7. customThe crude product was purified by chromatography on EM silica gel 60 (2.75×25 cm column)
  8. washeluting with 5% EtOAc in CH2Cl2

Sources & evidence

ORD record
ord-a367a408430944bbb08399596fe2ba10
Source dataset
uspto-grants-2007_01
Patent number
US07157604B2

Reaction notes

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