Hydrochloric Acid → HCID 44479641, compound

HRID 44194Notes

Reaction equation

HRID 44194 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]3[C:14]4=[C:15]([CH2:17][CH2:18][N:13]4[C:12](=O)[CH2:11][CH2:10]3)[CH:16]=2)[CH:2]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:29])=CC=1.Cl>C1(C)C=CC=CC=1.C1COCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]3[C:14]4=[C:15]([CH2:17][CH2:18][N:13]4[C:12](=[S:29])[CH2:11][CH2:10]3)[CH:16]=2)[CH:2]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 87949Lawesson's reagentHCID 44479388HCID 44479388, compound

Product 1

HCID 44479641HCID 44479641, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 8-pyridin-3-yl-1,2,5,6-tetrahydro-pyrrolo[3,2,1-ij]quinoline-4-one (900 mg, 3.60 mmol) and Lawessons reagent (1.45 g, 3.60 mmol) was refluxed in a mixture of 50 ml toluene and 5 ml THF for 2 h. After evaporation of the solvent under reduced pressure, the residue was purified by flash chromatography on silica gel (hexanes/ethyl acetate, 1/1, Rf=0.25). 8-Pyridin-3-yl-1,2,5,6-tetrahydro-pyrrolo[3,2,1-ij]quinoline-4-thione was obtained as a yellow solid (155 mg, 0.58 mmol, 26%), mp (HCl salt, THF) 283° C. 1H-NMR (500 MHz, CDCl3): δ=2.96 (t, 3J=7.9 Hz, 2H), 3.25 (t, 3J=7.6 Hz, 2H), 3.29 (t, 3J=8.0 Hz, 2H), 4.42 (t, 3J=8.2 Hz, 2H), 7.23 (s, 1H), 7.33 (s, 1H), 7.34 (ddd, 3J=7.9 Hz, 3J=4.7 Hz, 5J=0.6 Hz, 1H), 7.81 (ddd, 3J=7.9 Hz, 4J=2.5 Hz, 4J=1.9 Hz, 1H), 8.57 (dd, 3J=4.7 Hz, 4J=1.6 Hz, 1H), 8.59 (d, 4J=2.2 Hz, 1H). 13C-NMR (125 MHz, CDCl3): δ=23.5, 27.1, 40.3, 52.0, 122.7, 123.0, 123.6, 125.1, 131.7, 134.2, 135.2, 136.4, 139.6, 148.1, 148.5, 192.5. MS m/z 267.10 (MH+).

Workup

  1. customAfter evaporation of the solvent under reduced pressure
  2. customthe residue was purified by flash chromatography on silica gel (hexanes/ethyl acetate, 1/1, Rf=0.25)

Sources & evidence

ORD record
ord-cca007bc27104c16853460cd7e7334da
Source dataset
uspto-grants-2013_09
Patent number
US08541404B2

Reaction notes

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