Tributylstannane → 5-chloro-3,4-dihydroquinolin-2(1H)-one

HRID 1521645Notes

Reaction equation

HRID 1521645 reaction equation
[Cl:1][C:2]1[C:3](I)=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].CC(N=NC(C#N)(C)C)(C#N)C.C([SnH](CCCC)CCCC)CCC.C([O:37][C:38](=O)[CH:39]=[CH2:40])C>CS(C)=O>[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:4]2[C:3]=1[CH2:40][CH2:39][C:38](=[O:37])[NH:5]2

Participants

6

Reactant 4

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 8821Ethyl AcrylateHCID 213289463-Chloro-2-iodoaniline

Product 1

HCID 190277365-chloro-3,4-dihydroquinolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred solution of 3-chloro-2-iodoaniline (143-3; 1.1 g, 0.0043 mol), AIBN (0.282 g, 0.0017 mol), tributyl tinhydride (1.8 g, 0.0064 mol) in dimethyl sulphoxide (10 mL) was added ethylacrylate (1.7 g, 0.173 mol) portion wise at 0° C. Reaction mixture was allowed to stir at 120° C. for 12 h. The reaction mixture was diluted with ice cold water (150 mL) and extracted with ethyl acetate (4×100 mL). The combined organic layer was washed with saturated aqueous sodium chloride solution, dried over sodium sulphate and concentrated under vacuum to obtain the title compound. 1H NMR (400 MHz, CDCl3) δ 7.159-7.119 (t, J=7.6 Hz, 1H), 7.021-7.002 (d, J=7.6 Hz, 1H), 6.819-6.800 (d, J=7.6 Hz, 1H), 2.941-2.651 (t, J=8 Hz, 4H). MS (M+1): 181.8.

Workup

  1. customReaction mixture
  2. extractionextracted with ethyl acetate (4×100 mL)
  3. washThe combined organic layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-2f15a7fe4ec9439ea998c3a5649177e8
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

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