Potassium Hydroxide → HCID 6216654, compound

HRID 1162170Notes

Reaction equation

HRID 1162170 reaction equation
[CH3:1][C:2]1([CH3:20])[CH2:11][C:10]2[N:9]=[CH:8][C:7]3[NH:12][C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=4[C:6]=3[C:5]=2[C:4](=O)[CH2:3]1.O.NN.[OH-].[K+]>C(O)CO>[CH3:1][C:2]1([CH3:20])[CH2:11][C:10]2[N:9]=[CH:8][C:7]3[NH:12][C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=4[C:6]=3[C:5]=2[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 12074914HCID 12074914, compound

Product 1

HCID 6216654HCID 6216654, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

3,3-Dimethyl-2,3,4,7-tetrahydroindolo[2,3-c]quinolin-1-one of Example 1h (1.36 g, 5.14 mmol) was added to a mixture of ethylene glycol (8 mL) and hydrazine monohydrate (5 mL) at room temperature under stirring. The mixture was refluxed for 1 h, cooled, potassium hydroxide (1 g) was added, and the reaction mixture was refluxed for 2 h. The excess of hydrazine and water was slowly distilled off at 1 psi until the vapor temperature reached 190° C. The residue was cooled, diluted with water (60 mL), and the solid product was filtered off, washed with water and recrystallized from ethanol-water, 1:1. The product was isolated as colorless solid (0.59 g, 46%). Crystallization from toluene yielded the analytically pure sample; m.p. 275-277° C. 1H NMR (DMSO-d6) δ 1.03 (s, 6H), 1.72 (t, 2H), 2.76 (s, 2H), 3.30 (t, 2H), 7.20-7.23 (m, 1H), 7.49-7.60 (m, 2H), 8.17 (d, 1H), 8.66 (s, 1H), 11.45 (s, 1H).

Workup

  1. temperatureThe mixture was refluxed for 1 h
  2. temperaturecooled
  3. temperaturethe reaction mixture was refluxed for 2 h
  4. distillationThe excess of hydrazine and water was slowly distilled off at 1 psi until the vapor temperature
  5. customreached 190° C
  6. temperatureThe residue was cooled
  7. additiondiluted with water (60 mL)
  8. filtrationthe solid product was filtered off
  9. washwashed with water
  10. customrecrystallized from ethanol-water, 1:1

Sources & evidence

ORD record
ord-d77d7d0d379b44a398d8ce6d84ae0818
Source dataset
uspto-grants-2010_10
Patent number
US07820691B2

Reaction notes

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