Triethylsilane → 5,6-dihydro-5-oxo-11H-indeno [1,2-c]isoquinoline

HRID 2306567Notes

Reaction equation

HRID 2306567 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]2[C:12](=O)[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[C:4]=2[NH:3]1.C([SiH](CC)CC)C.CO.C(Cl)Cl>FC(F)(F)C(O)=O>[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]2[CH2:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[C:4]=2[NH:3]1

Participants

5

Reactant 3

HCID 12052TriethylsilaneHCID 13802540HCID 13802540, compoundHCID 21226129Dichloromethane methanol

Product 1

HCID 101053885,6-dihydro-5-oxo-11H-indeno [1,2-c]isoquinolineYield 88.7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a stirred suspension of 2 (40 g, 0.16 mol) in trifluoroacetic acid (2.5 L) was added triethylsilane (94 g, 0.8 mol) in small portions at room temperature and the reaction mixture was stirred for 96 h, during which time the reaction progress was monitored using TLC (eluent −5% MeOH/CH2Cl2). The reaction mixture was slowly poured on ice, filtered, washed with copious amounts of H2O and MeOH and dried in vacuo to provide the above-titled compound 6 (33.1 g, 88%), whose spectral data were identical to those of a sample of compound 6 that was obtained using Method I.

Workup

  1. additionThe reaction mixture was slowly poured on ice
  2. filtrationfiltered
  3. washwashed with copious amounts of H2O and MeOH
  4. customdried in vacuo

Sources & evidence

ORD record
ord-bd79d371148a42329cb390f2c6c3bd85
Source dataset
uspto-grants-2004_12
Patent number
US06828319B2

Reaction notes

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