Ammonium Chloride → 2-Di-n-propylamino-8-[2[(isopropylideneamino)oxy]benzoyl]-1,2,3,4-tetrahydronaphthalene

HRID 1899595Notes

Reaction equation

HRID 1899595 reaction equation
[CH3:1][C:2](=[N:4][OH:5])[CH3:3].CC(C)([O-])C.[K+].[CH2:12]([N:15]([CH2:35][CH2:36][CH3:37])[CH:16]1[CH2:25][CH2:24][C:23]2[C:18](=[C:19]([C:26](=[O:34])[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3F)[CH:20]=[CH:21][CH:22]=2)[CH2:17]1)[CH2:13][CH3:14].[Cl-].[NH4+]>C1COCC1>[CH2:35]([N:15]([CH2:12][CH2:13][CH3:14])[CH:16]1[CH2:25][CH2:24][C:23]2[C:18](=[C:19]([C:26](=[O:34])[C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:32]=3[O:5][N:4]=[C:2]([CH3:3])[CH3:1])[CH:20]=[CH:21][CH:22]=2)[CH2:17]1)[CH2:36][CH3:37]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 67180Acetone, oximeHCID 152335372-Di-n-propylamino-8-(2'-fluorobenzoyl)-1,2,3,4-tetrahydronaphthaleneHCID 23665647Potassium tert-butoxide

Product 1

HCID 233735352-Di-n-propylamino-8-[2[(isopropylideneamino)oxy]benzoyl]-1,2,3,4-tetrahydronaphthaleneYield 142%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 47.5 mg of acetone oxime (0.65 mmol) in 25 ml of THF were added 73 mg (0.65 mmol) of potassium t-butoxide. The mixture was stirred at room temperature for one hour after which 210 mg of 2-di-n-propylamino-8-(2'-fluorobenzoyl)-1,2,3,4-tetrahydronaphthalene in THF were added via a syringe. The resulting mixture was refluxed for three hours after which it was cooled and poured into an aqueous solution of ammonium chloride. The mixture then was extracted with either, and the extract was dried and concentrated to obtain 343 mg of 2-di-n-propylamino-8-[2[(isopropylideneamino)oxy]benzoyl]-1,2,3,4-tetrahydronaphthalene.

Workup

  1. additionwere added via a syringe
  2. temperatureThe resulting mixture was refluxed for three hours after which it
  3. temperaturewas cooled
  4. extractionThe mixture then was extracted with either, and the extract
  5. customwas dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f3283b41c6864ae299294209da1d7212
Source dataset
uspto-grants-1996_11
Patent number
US05571942

Reaction notes

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