Tetrahydrofuran → HCID 53392262, compound

HRID 1922468Notes

Reaction equation

HRID 1922468 reaction equation
[CH2:1]([N:3]([CH2:20][CH3:21])[CH2:4][CH2:5][N:6]1[C:15]2[C:10](=[CH:11][C:12]([N+:16]([O-:18])=[O:17])=[CH:13][CH:14]=2)[CH2:9][CH2:8][C:7]1=O)[CH3:2].C1COCC1>CO>[CH2:20]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][N:6]1[C:15]2[C:10](=[CH:11][C:12]([N+:16]([O-:18])=[O:17])=[CH:13][CH:14]=2)[CH2:9][CH2:8][CH2:7]1)[CH3:21]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 53392092HCID 53392092, compound

Product 1

HCID 53392262HCID 53392262, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 1-(2-(diethylamino)ethyl)-6-nitro-3,4-dihydroquinolin-2(1H)-one (1 g, 3.43 mmol) and 1M BH3 in THF (17.16 ml, 17.16 mmol) was stirred at room temperature overnight. After this time, the reaction was cooled to 0° C. then treated with methanol (25 mL) dropwise with caution. The mixture was stirred at 0° C. for 10 minutes then concentrated on the rotovap to give a yellow solid. This compound was dissolved in 40 mL methanol and heated at reflux for 3 hours. After cooling, the solvent was evaporated and the resulting yellow brown residue was subjected to flash chromatography on silica gel using 5% 2M NH3 in methanol/95% CH2Cl2 to give a bright yellow residue (0.87 g, 91%). 1H-NMR (CDCl3) δ 7.96 (dd, J=2.7, 9.0 Hz, 1H), 7.85-7.84 (m, 1H), 6.51 (d, J=9.0 Hz, 1H), 3.47 (t, J=5.4 Hz, 4H), 2.74 (t, J=6.3 Hz, 2H), 2.68-2.59 (m, 6H), 1.99-1.91 (m, 2H), 1.05 (t, J=6.9 Hz, 6H). MS (ESI): 278.2 (M+1).

Workup

  1. concentrationthen concentrated on the rotovap
  2. customto give a yellow solid
  3. temperatureheated
  4. temperatureat reflux for 3 hours
  5. temperatureAfter cooling
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-0f7a92f4316d4c7eafef6998c9ad799d
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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