Hydroxylamine → 2-Di-n-propylamino-8-(4-ethylisoxazol-5-yl)-1,2,3,4-tetrahydronaphthalene

HRID 1647832Notes

Reaction equation

HRID 1647832 reaction equation
C[C:2]([CH3:5])([O-])C.[K+].C(O[CH2:10][CH3:11])=O.[CH2:12]([N:15]([CH2:31][CH2:32][CH3:33])[CH:16]1[CH2:25][CH2:24][C:23]2[C:18](=[C:19]([C:26](=O)CCC)C=CC=2)C1)[CH2:13][CH3:14].[NH2:34]O.[OH-].[NH4+].[O:38]1[CH2:42][CH2:41][CH2:40][CH2:39]1>O>[CH2:31]([N:15]([CH2:12][CH2:13][CH3:14])[CH:16]1[CH2:25][CH2:24][C:23]2[C:40](=[C:41]([C:42]3[O:38][N:34]=[CH:2][C:5]=3[CH2:10][CH3:11])[CH:26]=[CH:19][CH:18]=2)[CH2:39]1)[CH2:32][CH3:33]

Participants

8

Reactant 6

HCID 787HydroxylamineHCID 8025Ethyl formateHCID 8028Tetrahydrofuran2×HCID 14923Ammonium HydroxideHCID 152335322-(Di-n-propylamino)-8-butyryl-1,2,3,4-tetrahydronaphthaleneHCID 23665647Potassium tert-butoxide

Product 1

HCID 233735222-Di-n-propylamino-8-(4-ethylisoxazol-5-yl)-1,2,3,4-tetrahydronaphthalene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Potassium t-butoxide (0.82 g; 7.3 mmol) was suspended in 100 ml of tetrahydrofuran (THF). Ethyl formate (1.0 g; 13.3 mmool) and 2-(Di-n-propylamino)-8-butyryl-1,2,3,4-tetrahydronaphthalene (1.0 g; 3.3 mmol) in THF were added to the mixture. The resulting mixture was stirred at room temperature overnight. Hydroxylamine (1.2 g; 16.6 mmol) was added followed by sufficient water to dissolve the solid. The resulting mixture, having pH 6, was stirred at room temperature for 20 hours after which it was poured into water, and the pH was adjusted to 12 with ammonium hydroxide. The mixture was then extracted with methylene chloride. The extract was dried over sodium sulfate and evaporated. The residue was dissolved in 100 mg of toluene, and 100 mg of p-toluenesulfonic acid was added. The mixture then was refluxed for 1.5 hours after which it was poured into water and extracted with methylene chloride. The methylene chloride extract was dried over sodium sulfate and evaporated.

Workup

  1. dissolutionto dissolve the solid
  2. stirringwas stirred at room temperature for 20 hours after which it
  3. extractionThe mixture was then extracted with methylene chloride
  4. dry with materialThe extract was dried over sodium sulfate
  5. customevaporated
  6. dissolutionThe residue was dissolved in 100 mg of toluene
  7. addition100 mg of p-toluenesulfonic acid was added
  8. temperatureThe mixture then was refluxed for 1.5 hours after which it
  9. additionwas poured into water
  10. extractionextracted with methylene chloride
  11. extractionThe methylene chloride extract
  12. dry with materialwas dried over sodium sulfate
  13. customevaporated

Sources & evidence

ORD record
ord-c0cb29ffc732425ba9c4c288becdc0a5
Source dataset
uspto-grants-1995_07
Patent number
US05434174

Reaction notes

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