Water → HCID 86698030, compound

HRID 518883Notes

Reaction equation

HRID 518883 reaction equation
[N-:1]=[N+]=[N-].[Na+].[CH3:5][CH:6]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH2:13][CH2:14][CH2:15][C:16]2=[O:19])=[CH:11][CH:10]=1)[CH3:7].O.C(=O)([O-])[O-].[Na+].[Na+]>FC(F)(F)C(O)=O>[CH3:5][CH:6]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[CH2:13][CH2:14][CH2:15][C:16](=[O:19])[NH:1][C:17]=2[CH:18]=1)[CH3:7]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 33557Sodium AzideHCID 142567607-Isopropoxy-3,4-dihydronaphthalen-1(2H)-one

Product 1

HCID 86698030HCID 86698030, compoundYield 14.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

900 mg of sodium azide are added at ambient temperature to a solution of 2.24 g of 7-(propan-2-yloxy)-3,4-dihydronaphthalen-1(2H)-one in 35 ml of trifluoroacetic acid. The reaction medium is refluxed for 3 hours and is then brought back to ambient temperature. The reaction medium is poured into 100 ml of water and the pH is adjusted to pH 7 by adding sodium carbonate. The mixture is extracted twice with 100 ml of ethyl acetate. The combined organic phases are dried over magnesium sulfate, filtered and evaporated. The residue is purified by flash chromatography on silica gel, elution being carried out with dichloromethane and then a dichloromethane/methanol (9/1) mixture, so as to obtain 346 mg of 8-(propan-2-yloxy)-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one in the form of an orangey-coloured oil.

Workup

  1. temperatureThe reaction medium is refluxed for 3 hours
  2. customis then brought back to ambient temperature
  3. extractionThe mixture is extracted twice with 100 ml of ethyl acetate
  4. dry with materialThe combined organic phases are dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is purified by flash chromatography on silica gel, elution

Sources & evidence

ORD record
ord-8e8461cd1d6e488185faff2c5c20f301
Source dataset
uspto-grants-2015_08
Patent number
US09115140B2

Reaction notes

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