Hydroxyamine hydrochloride → HCID 86741127, compound

HRID 978715Notes

Reaction equation

HRID 978715 reaction equation
[CH3:1][C:2]1([CH3:17])[CH2:15][CH2:14][N:5]2[C:6]3[C:11]([C:12]([CH3:13])=[C:4]2[C:3]1=O)=[CH:10][CH:9]=[CH:8][CH:7]=3.Cl.[NH2:19][OH:20]>N1C=CC=CC=1>[CH3:1][C:2]1([CH3:17])[CH2:15][CH2:14][N:5]2[C:6]3[C:11]([C:12]([CH3:13])=[C:4]2[C:3]1=[N:19][OH:20])=[CH:10][CH:9]=[CH:8][CH:7]=3

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 13749124HCID 13749124, compound

Product 1

HCID 86741127HCID 86741127, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The title compound is prepared in an analogous manner to Step 1. A mixture of 6,7,8,9-tetrahydro-8,8,10-trimethylpyrido[1,2-a]indol-9-one (700 mg, 3.08 mmol, described in Example 1, Step 3), and hydroxylamine hydrochloride (420 mg, 6.04 mmol) was refluxed in pyridine (40 mL) for 21/2 hours. The reaction mixture was evaporated to dryness in vacuo and the residue suspended in water (20 mL). The insoluble components were extracted with ether (3×40 mL). The combined organic layer was washed with 5% hydrochloric acid, 10% sodium bicarbonate, and water. The separated organic layer was dried over MgSO4, filtered, and evaporated. The residue was chromatographed on silica gel (10 g). Elution with chloroform/hexane (1:1) afforded 300 mg (40%) of the title compound as a yellow oil.

Workup

  1. customThe title compound is prepared in an analogous manner to Step 1
  2. customThe reaction mixture was evaporated to dryness in vacuo
  3. extractionThe insoluble components were extracted with ether (3×40 mL)
  4. washThe combined organic layer was washed with 5% hydrochloric acid, 10% sodium bicarbonate, and water
  5. dry with materialThe separated organic layer was dried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was chromatographed on silica gel (10 g)
  9. washElution with chloroform/hexane (1:1)

Sources & evidence

ORD record
ord-b0ef9f161e2d49c9a3ef288bba89aaaf
Source dataset
uspto-grants-1987_05
Patent number
US04665183

Reaction notes

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