Tetrahydrofuran → HCID 59807100, compound

HRID 1922510Notes

Reaction equation

HRID 1922510 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([CH3:22])[CH2:5][CH2:6][CH2:7][N:8]1[C:17]2[C:12](=[CH:13][C:14]([N+:18]([O-:20])=[O:19])=[CH:15][CH:16]=2)[CH2:11][CH2:10][C:9]1=O.C1COCC1>>[CH3:22][N:4]([CH2:5][CH2:6][CH2:7][N:8]1[C:17]2[C:12](=[CH:13][C:14]([N+:18]([O-:20])=[O:19])=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1)[CH2:3][CH2:2][OH:1]

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 59807141HCID 59807141, compound

Product 1

HCID 59807100HCID 59807100, compound

Conditions

Temperature
60 °C

Procedure

1-(3-((2-Hydroxyethyl)(methyl)amino)propyl)-6-nitro-3,4-dihydroquinolin-2(1H)-one (200 mg, 0.651 mmol) was stirred in borane-tetrahydrofuran complex, 1M sol'n in THF (6.507 mL, 6.51 mmol) until the material dissolved. The resulting solution was then heated at 60° C. overnight. The reaction mixture was then cooled in an ice bath and quenched with methanol (slowly). The solution was then concentrated, redissolved in methanol (5 mL) and stirred with 1M HCl (5 mL) at reflux for 1 h. The mixture was then basified with 1M NaOH and extracted with dichloromethane (3×). The combined organics were dried, filtered and concentrated, then chromatographed on silica gel eluting with ethyl acetate, followed by 5% (2M NH3/methanol) in dichloromethane. 1H NMR (DMSO-d6) δ 7.88 (dd, J=9.3, 2.7 Hz, 1H), 7.77 (d, J=2.7 Hz, 1H), 6.72 (d, J=9.3 Hz, 1H), 4.40 (t, J=5.4 Hz, 1H), 3.51-3.32 (m, 6H), 2.74 (t, J=6 Hz, 2H), 2.41-2.33 (m, 4H), 1.89-1.81 (m, 2H), 1.72-1.64 (m, 2H).

Workup

  1. temperatureThe reaction mixture was then cooled in an ice bath
  2. customquenched with methanol (slowly)
  3. concentrationThe solution was then concentrated
  4. dissolutionredissolved in methanol (5 mL)
  5. temperatureat reflux for 1 h
  6. extractionextracted with dichloromethane (3×)
  7. customThe combined organics were dried
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customchromatographed on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-fdc828c58258491f9bb88c17b90bf2c5
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

Loading…