(Dimethyl sulfide)trihydroboron → HCID 59441825, compound

HRID 1014379Notes

Reaction equation

HRID 1014379 reaction equation
[CH3:1][C:2]1([CH3:18])[C:11]2[C:6](=[CH:7][C:8]([N+:14]([O-:16])=[O:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[NH:5][C:4](=O)[CH2:3]1.B.CSC>O1CCCC1>[CH3:1][C:2]1([CH3:18])[C:11]2[C:6](=[CH:7][C:8]([N+:14]([O-:16])=[O:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[NH:5][CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 59441860HCID 59441860, compound

Product 1

HCID 59441825HCID 59441825, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4,4-dimethyl-6-(methyloxy)-7-nitro-3,4-dihydro-2(1H)-quinolinone (2.5 g, 10 mmol) in tetrahydrofuran (45 mL) was treated with borane-dimethylsulfide complex (20.5 mL, 41 mmol, 2 M in THF, Acros Organics). The mixture was heated at reflux for 16 h, cooled, quenched carefully via dropwise of excess methanol, concentrated, and purified by column chromatography on SiO2 (0 to 100% ethyl acetate/dichloromethane) to obtain 4,4-dimethyl-6-(methyloxy)-7-nitro-1,2,3,4-tetrahydroquinoline (1.33 g, 5.63 mmol, 56%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.26 (s, 6 H), 1.58-1.65 (m, 2 H), 3.13-3.21 (m, 2 H), 3.79 (s, 3 H), 5.95 (bs, 1 H), 6.96 (s, 1 H), 7.06 (s, 1 H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 16 h
  3. temperaturecooled
  4. customquenched carefully via dropwise of excess methanol
  5. concentrationconcentrated
  6. custompurified by column chromatography on SiO2 (0 to 100% ethyl acetate/dichloromethane)

Sources & evidence

ORD record
ord-5a211fd1ff1642b1ad044731592ad71a
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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