Potassium Nitrate → HCID 86698001, compound

HRID 518840Notes

Reaction equation

HRID 518840 reaction equation
[N+:1]([O-:4])([O-])=[O:2].[K+].[CH3:6][CH:7]([O:9][C:10]1[C:15]2[CH2:16][CH2:17][CH2:18][C:19](=[O:21])[NH:20][C:14]=2[CH:13]=[CH:12][CH:11]=1)[CH3:8].C(=O)(O)[O-].[Na+]>FC(F)(F)C(OC(=O)C(F)(F)F)=O>[N+:1]([C:11]1[CH:12]=[CH:13][C:14]2[NH:20][C:19](=[O:21])[CH2:18][CH2:17][CH2:16][C:15]=2[C:10]=1[O:9][CH:7]([CH3:8])[CH3:6])([O-:4])=[O:2]

Participants

5

Reactant 3

HCID 24434Potassium NitrateHCID 516892Sodium BicarbonateHCID 86698000HCID 86698000, compound

Product 1

HCID 86698001HCID 86698001, compoundYield 28.7%

Reagents, catalysts & solvents 1

HCID 9845Trifluoroacetic anhydrideSolvent

Conditions

Temperature
-5 °C

Procedure

750 mg of potassium nitrate are added, in portions, to a solution of 1.3 g of 6-(propan-2-yloxy)-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one in 13 ml of trifluoroacetic anhydride brought back to −5° C. The reaction medium is stirred for 5 minutes at −5° C. and then brought back to pH 5 by adding a saturated aqueous sodium bicarbonate solution. The mixture is extracted with ethyl acetate and the organic phase is dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification is carried out by flash chromatography on silica gel (40-63 μm), elution being carried out with a mixture of heptane and of ethyl acetate (80/20 to 50/50). 450 mg of 7-nitro-6-(propan-2-yloxy)-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one are obtained in the form of a beige solid. 91 mg of sodium hydride at 50% are added to a solution of 445 mg of 7-nitro-6-(propan-2-yloxy)-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one in 10 ml of DMF. The reaction medium is stirred for 10 minutes at ambient temperature and then 263 mg of iodomethane are added. The reaction medium is stirred for 1 hour at ambient temperature, poured into ice-cold water and extracted with ethyl acetate. The organic phase is dried over magnesium sulfate, filtered and evaporated under reduced pressure, so as to give 417 mg of 1-methyl-7-nitro-6-(propan-2-yloxy)-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one in the form of a yellow gum.

Workup

  1. custombrought back to −5° C
  2. extractionThe mixture is extracted with ethyl acetate
  3. dry with materialthe organic phase is dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification
  7. washis carried out by flash chromatography on silica gel (40-63 μm), elution
  8. additionbeing carried out with a mixture of heptane and of ethyl acetate (80/20 to 50/50)

Sources & evidence

ORD record
ord-984377dda611464f8b6469b11aa80b80
Source dataset
uspto-grants-2015_08
Patent number
US09115140B2

Reaction notes

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