HCID 19769437, compound → HCID 67785330, compound

HRID 1590036Notes

Reaction equation

HRID 1590036 reaction equation
[CH3:1][O:2][C:3]1[C:22]([O:23][CH3:24])=[CH:21][C:6]2[CH:7]([O:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:8][N:9]([N:12]=O)[CH2:10][CH2:11][C:5]=2[CH:4]=1.[C:25]([OH:28])(=[O:27])[CH3:26].[OH2:29]>[Zn]>[C:22]([OH:23])(=[O:29])/[CH:3]=[CH:26]\[C:25]([OH:28])=[O:27].[NH2:12][N:9]1[CH2:8][CH:7]([O:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:6]2[CH:21]=[C:22]([O:23][CH3:24])[C:3]([O:2][CH3:1])=[CH:4][C:5]=2[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 19769437HCID 19769437, compoundHCID 21899381Acetic acid--water (1/1)

Product 1

HCID 67785330HCID 67785330, compound

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

Zinc dust (9 g) was added to a solution of 7,8-dimethoxy-3-nitroso-1-phenoxy-2,3,4,5-tetrahydro-3-benzazepine (10 g) in 150 ml of 2:1 acetic acid/water. After stirring at ambient temperate for three hours, the reaction mixture was filtered, stirred with ice and basified with ammonium hydroxide. The oil which had separated was extracted with dichloromethane. The organic extract was washed with water and saturated sodium chloride solution, and thereafter dried (anhydrous magnesium sulfate), filtered and concentrated to 10 g brown oil. This was eluted through silica with ethyl acetate via high performance liquid chromatography to yield 8.6 g white solid, mp 98°-100°. This solid was again eluted through silica with 5% methanol in dichloromethane via high performance liquid chromatography to yield 6 g white solid, mp 107°-109°. A three gram portion was converted to the maleate salt in 10% methanol/ether to yield 3.3 g white solid, mp 132°-134°.

Workup

  1. filtrationthe reaction mixture was filtered
  2. stirringstirred with ice and basified with ammonium hydroxide
  3. customThe oil which had separated
  4. extractionwas extracted with dichloromethane
  5. extractionThe organic extract
  6. washwas washed with water and saturated sodium chloride solution
  7. dry with materialdried (anhydrous magnesium sulfate)
  8. filtrationfiltered
  9. concentrationconcentrated to 10 g brown oil
  10. washThis was eluted through silica with ethyl acetate via high performance liquid chromatography

Sources & evidence

ORD record
ord-29b4484b0b6942b1be94521be0d8e342
Source dataset
uspto-grants-1993_04
Patent number
US05202319

Reaction notes

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