Tetrahydrofuran → HCID 59807091, compound

HRID 1922517Notes

Reaction equation

HRID 1922517 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][CH2:9][N:10]2[C:19]3[C:14](=[CH:15][C:16]([N+:20]([O-:22])=[O:21])=[CH:17][CH:18]=3)[CH2:13][CH2:12][C:11]2=O)[CH2:3][CH2:2]1.C1COCC1>>[N+:20]([C:16]1[CH:15]=[C:14]2[C:19](=[CH:18][CH:17]=1)[N:10]([CH2:9][CH2:8][CH2:7][N:4]1[CH2:3][CH2:2][O:1][CH2:6][CH2:5]1)[CH2:11][CH2:12][CH2:13]2)([O-:22])=[O:21]

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 59807103HCID 59807103, compound

Product 1

HCID 59807091HCID 59807091, compoundYield 49.4%

Conditions

Temperature
0 °C

Procedure

1-(3-Morpholinopropyl)-6-nitro-3,4-dihydroquinolin-2(1H)-one (550 mg, 1.722 mmol) was stirred in borane tetrahydrofuran complex, 1M in THF (17.200 mL, 17.20 mmol) overnight at reflux temperature. The reaction mixture was then cooled to 0° C. and quenched via addition of methanol (10 mL). The solution was then concentrated, and the residue was redissolved in a small amount of methanol and stirred at reflux with 2N HCl for 2 h. The mixture was then neutralized and basified with 3N NaOH and extracted with dichloromethane (3×). The combined organics were dried, filtered and concentrated, then chromatographed in ethyl acetate, followed by 5-10% (2M NH3 in methanol) in dichloromethane, giving the desired 4-(3-(6-nitro-3,4-dihydroquinolin-1(2H)-yl)propyl)morpholine (260 mg, 0.851 mmol, 49.4% yield). 1H NMR (DMSO-d6) δ 7.87 (dd, J=9.3, 2.7 Hz, 1H), 7.77 (d, J=2.7 Hz, 1H), 6.72 (d, J=9.3 Hz, 1H), 3.60-3.56 (m, 4H), 3.45-3.39 (m, 4H), 2.74 (t, J=6 Hz, 2H), 2.35-2.26 (m, 6H), 1.88-1.80 (m, 2H), 1.76-1.66 (m, 2H).

Workup

  1. customquenched via addition of methanol (10 mL)
  2. concentrationThe solution was then concentrated
  3. dissolutionthe residue was redissolved in a small amount of methanol
  4. temperatureat reflux with 2N HCl for 2 h
  5. extractionextracted with dichloromethane (3×)
  6. customThe combined organics were dried
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customchromatographed in ethyl acetate

Sources & evidence

ORD record
ord-6856b684e2ae4024a0199d8dd803c77a
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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