Potassium Hydroxide → HCID 90016528, compound

HRID 1484426Notes

Reaction equation

HRID 1484426 reaction equation
C([N:6]1[CH2:33][CH2:32][C:9]2[N:10]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:11]3[CH:12]=[CH:13][C:14]([C:17]4[CH:18]=[C:19]([CH3:23])[CH:20]=[CH:21][CH:22]=4)=[CH:15][C:16]=3[C:8]=2[CH2:7]1)(OCC)=O.[OH-].[K+]>C(O)C>[C:19]1([CH3:23])[CH:20]=[CH:21][CH:22]=[C:17]([C:14]2[CH:13]=[CH:12][C:11]3[N:10]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:9]4[CH2:32][CH2:33][NH:6][CH2:7][C:8]=4[C:16]=3[CH:15]=2)[CH:18]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 90016647HCID 90016647, compound

Product 1

HCID 90016528HCID 90016528, compoundYield 63.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To the solution of 2-carbethoxy-8-m-tolyl-5-n-octyl-1,2,3,4-tetrahydropyrido[4,3-b]indole (7) in ethanol was added the aqueous solution of potassium hydroxide. The mixture was refluxed for 16 h. The reaction mixture was concentrated to remove ethanol and extracted with DCM for three times (15 mL×3). The DCM layer was washed with brine, dried with Na2SO4, filtered and concentrated to give brow residue. This residue was purified by silica gel column chromatography to give yellow oil. Yield: 63.6%. 1H NMR (300 Hz, CDCl3) δ 7.62 (br, 1H), 7.48-7.41 (m, 3H), 7.36-7.32 (m, 2H), 7.15-7.12 (m, 1H), 4.12 (br, 2H), 3.99 (t, 2H, J=7.2 Hz), 3.31 (br, 2H), 2.91 (br, 1H), 2.79 (br, 2H), 2.45 (s, 3H), 1.77-1.73 (m, 2H), 1.32-1.28 (s, 10H), 0.90 (t, 3H, J=6.6 Hz). 13C NMR (75 Hz, CDCl3) δ 142.57, 138.05, 135.45, 133.83, 132.48, 128.46, 128.06, 126.89, 125.91, 124.37, 120.56, 116.20, 109.13, 108.09, 43.26, 43.01, 42.14, 31.75, 30.35, 29.28, 29.14, 27.05, 23.10, 22.56, 21.55, 14.03.

Workup

  1. temperatureThe mixture was refluxed for 16 h
  2. concentrationThe reaction mixture was concentrated
  3. customto remove ethanol
  4. extractionextracted with DCM for three times (15 mL×3)
  5. washThe DCM layer was washed with brine
  6. dry with materialdried with Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give brow residue
  10. customThis residue was purified by silica gel column chromatography
  11. customto give yellow oil

Sources & evidence

ORD record
ord-b9af527287fe40929a10adbe613ca795
Source dataset
uspto-grants-2016_08
Patent number
US09422238B2

Reaction notes

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