Dimethyl Sulfide → HCID 59441908, compound

HRID 1014293Notes

Reaction equation

HRID 1014293 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[NH:9][C:8](=O)[CH2:7][CH2:6]2.CSC>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[NH:9][CH2:8][CH2:7][CH2:6]2

Participants

4

Reactant 2

HCID 1068Dimethyl SulfideHCID 109440476-Methoxy-7-nitro-1,2,3,4-tetrahydroquinolin-2-one

Product 1

HCID 59441908HCID 59441908, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 6-(methyloxy)-7-nitro-3,4-dihydro-2(1H)-quinolinone (75 g of, 0.34 mol, 1 equiv) in THF (1L) was added BH3.DMS (10 M, 150 mL, 1.5 mol, 4.4equiv) dropwise at 25° C. After the addition, the mixture was stirred for 6 h at 60° C. The reaction was cooled and quenched with excess MeOH, concentration under reduced pressure and purified via chromatography on SiO2 t afford 6-(methyloxy)-7-nitro1,2,3,4-tetrahydroquinoline (51.5 g, 73% yield). 1H NMR (400 MHz, DMSO) δ 1.73-1.80 (m, 2 H), 2.71 (t, 2 H, J=6.4 Hz), 3.13-3.16 (m, 2 H), 3.75 (s, 3H), 5.83(br, 1 H), 6.88(s, 1 H), 6.95(s, 1 H).

Workup

  1. customdropwise at 25° C
  2. additionAfter the addition
  3. temperatureThe reaction was cooled
  4. customquenched with excess MeOH, concentration under reduced pressure
  5. custompurified via chromatography on SiO2

Sources & evidence

ORD record
ord-fa369460ed134fd69b73700e9f082295
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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