Hydroxyamine hydrochloride → HCID 86741127, compound

HRID 1732059Notes

Reaction equation

HRID 1732059 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-539f3dee0dea43faac8884edc9f217cd
Source dataset
uspto-grants-1986_11
Patent number
US04624954

Reaction notes

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