Hydroxyamine hydrochloride → HCID 86741128, compound

HRID 1732071Notes

Reaction equation

HRID 1732071 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH3:17])=[C:8]3[C:15](=O)[CH2:14][CH2:13][CH2:12][N:9]32)=[CH:5][CH:4]=1.Cl.[NH2:19][OH:20]>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH3:17])=[C:8]3[C:15](=[N:19][OH:20])[CH2:14][CH2:13][CH2:12][N:9]32)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 13749130HCID 13749130, compound

Product 1

HCID 86741128HCID 86741128, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 6,7,8,9-tetrahydro-3-methoxy-10-methylpyrido[1,2-a]indol-9-one (2.29 g, 10 mmol) and hydroxylamine hydrochloride (1.39 g, 20 mmol) in dry pyridine (40 mL) was refluxed for 2 hours. The reaction mixture was concentrated to 10% of its original volume and distilled water (80 mL) was added. The organic product was extracted with ether (3×60 mL). The combined organic layers were washed with water (100 mL), 5% hydrochloric acid (50 mL), and 10% sodium bicarbonate (50 mL). The separated organic layer was dried over MgSO4, filtered, and evaporated. The residue was recrystallized from methanol/water to afford 2.4 g (98%) of the title compound as gray microcrystals.

Workup

  1. concentrationThe reaction mixture was concentrated to 10% of its original volume
  2. distillationdistilled water (80 mL)
  3. additionwas added
  4. extractionThe organic product was extracted with ether (3×60 mL)
  5. washThe combined organic layers were washed with water (100 mL), 5% hydrochloric acid (50 mL), and 10% sodium bicarbonate (50 mL)
  6. dry with materialThe separated organic layer was dried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was recrystallized from methanol/water

Sources & evidence

ORD record
ord-b6694d89f6844b22b724ccdd1faaeef7
Source dataset
uspto-grants-1986_11
Patent number
US04624954

Reaction notes

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