Pyridine → HCID 136380319, compound

HRID 1162177Notes

Reaction equation

HRID 1162177 reaction equation
[CH3:1][CH:2]1[CH2:11][C:10]2[N:9]=[C:8]([CH3:12])[C:7]3[NH:13][C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=4[C:6]=3[C:5]=2[C:4](=O)[CH2:3]1.N1C=CC=CC=1.Cl.[NH2:28][OH:29]>C(O)C>[CH3:1][CH:2]1[CH2:11][C:10]2[N:9]=[C:8]([CH3:12])[C:7]3[NH:13][C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=4[C:6]=3[C:5]=2[C:4](=[N:28][OH:29])[CH2:3]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 24771131HCID 24771131, compound

Product 1

HCID 136380319HCID 136380319, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3,6-dimethyl-2,3,4,7-tetrahydroindolo[2,3-c]quinolin-1-one of Example 12 (0.26 g, 1 mmol), ethanol (4 mL), pyridine (0.15 mL, 1.85 mmol) and hydroxylamine hydrochloride (0.1 g, 1.5 mmol) was refluxed for 3 h. The mixture was cooled, the solid product was filtered off, washed with ethanol, dried, and dissolved in hot water (20 mL). Aqueous ammonium hydroxide was added to pH 9. The precipitate was collected, washed with water, dried and crystallized from ethanol-water, 1:1 to give 0.17 g (61%) of colorless crystals; m.p. 282-283° C.

Workup

  1. temperaturewas refluxed for 3 h
  2. temperatureThe mixture was cooled
  3. filtrationthe solid product was filtered off
  4. washwashed with ethanol
  5. customdried
  6. dissolutiondissolved in hot water (20 mL)
  7. additionAqueous ammonium hydroxide was added to pH 9
  8. customThe precipitate was collected
  9. washwashed with water
  10. customdried
  11. customcrystallized from ethanol-water, 1:1

Sources & evidence

ORD record
ord-8c514321b70d4552bade6f4043f02b6c
Source dataset
uspto-grants-2010_10
Patent number
US07820691B2

Reaction notes

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