Ammonium Hydroxide → HCID 74044273, compound

HRID 22146Notes

Reaction equation

HRID 22146 reaction equation
[CH2:1]([N:4]([CH2:20][CH2:21][CH3:22])[CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[C:8]([C:15](=O)[CH2:16][CH2:17][CH3:18])[CH:9]=[CH:10][CH:11]=2)[CH2:6]1)[CH2:2][CH3:3].Cl.[NH2:24][OH:25].[OH-].[NH4+]>CO.O>[CH2:1]([N:4]([CH2:20][CH2:21][CH3:22])[CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[C:8]([C:15](=[N:24][OH:25])[CH2:16][CH2:17][CH3:18])[CH:9]=[CH:10][CH:11]=2)[CH2:6]1)[CH2:2][CH3:3]

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 152335322-(Di-n-propylamino)-8-butyryl-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 74044273HCID 74044273, compoundYield 105.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

2-Di-n-propylamino-8-butyryl-1,2,3,4-tetrahydronaphthalene (1 g; 3.3 mmol) (prepared as in Example 22) was dissolved in 40 ml of methanol, and 2.3 g (33 mmol) of hydroxylamine hydrochloride dissolved in water were added. The mixture was stirred at room temperature for 20 hours after which it was poured into water, and the pH was adjusted to 10 using ammonium hydroxide. The mixture then was extracted with methylene chloride, and the extract was dried over sodium sulfate and evaporated. The residue was placed on a silica gel column and was eluted with a gradient mixture of 3-5% methanol in methylene chloride containing a trace of ammonium hydroxide. The appropriate fractions were combined and evaporated to give 1.1 g of 2-di-n-propylamino-8-(1-oximino-butyl)-1,2,3,4-tetrahydronaphthalene. (Rf=0.30 in 4% methanol and methylene chloride containing a trace of ammonium hydroxide) MS(FD): 316(100).

Workup

  1. additionwere added
  2. extractionThe mixture then was extracted with methylene chloride
  3. dry with materialthe extract was dried over sodium sulfate
  4. customevaporated
  5. washwas eluted with a gradient mixture of 3-5% methanol in methylene chloride containing a trace of ammonium hydroxide
  6. customevaporated

Sources & evidence

ORD record
ord-c5750bb9b0334dc6bff575aff2170b9f
Source dataset
uspto-grants-1995_06
Patent number
US05426226

Reaction notes

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