Water → 7-Chloro-1-(2,3-dihydroxypropyl)-5-(o-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one

HRID 1658442Notes

Reaction equation

HRID 1658442 reaction equation
[Mn]([O-])(=O)(=O)=[O:2].[K+].[CH2:7]([N:10]1[C:16]2[CH:17]=[CH:18][C:19]([Cl:21])=[CH:20][C:15]=2[C:14]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[F:28])=[N:13][CH2:12][C:11]1=[O:29])[CH:8]=[CH2:9].[OH2:30]>CC(C)=O>[Cl:21][C:19]1[CH:18]=[CH:17][C:16]2[N:10]([CH2:7][CH:8]([OH:2])[CH2:9][OH:30])[C:11](=[O:29])[CH2:12][N:13]=[C:14]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[F:28])[C:15]=2[CH:20]=1

Participants

5

Reactant 3

HCID 962WaterHCID 516875Potassium Permanganate2×HCID 21529372HCID 21529372, compound

Product 1

HCID 30504337-Chloro-1-(2,3-dihydroxypropyl)-5-(o-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 16 g of potassium permanganate in 300 ml of water was added dropwise within 15 minutes at 10°C to a solution of 33.0 g of 1-allyl-7-chloro-5-(2-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one in 300 ml of acetone. After the potassium permanganate addition, the solution is stirred for a further 10 minutes. Then the mixture is filtered off by vacuum from the precipitated manganese dioxide and the manganese dioxide is washed with acetone. Subsequently the acetone is distilled off on a rotary evaporator. The remaining aqueous phase is extracted with ethyl acetate; the ethyl acetate solution is washed with saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated. The residue is chromatographed on silica gel with ethyl acetate/methanol (9:1). The pure fractions are combined and evaporated. Crystallization from ethyl acetate yields pure 7-chloro-1-(2,3-dihydroxypropyl)-5-(2-fluorophenyl) -1,3-dihydro-2H-1,4-benzodiazepin-2-one of melting point 117°-118°C.

Workup

  1. filtrationThen the mixture is filtered off by vacuum from the precipitated manganese dioxide
  2. washthe manganese dioxide is washed with acetone
  3. distillationSubsequently the acetone is distilled off on a rotary evaporator
  4. extractionThe remaining aqueous phase is extracted with ethyl acetate
  5. washthe ethyl acetate solution is washed with saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue is chromatographed on silica gel with ethyl acetate/methanol (9:1)
  10. customevaporated
  11. customCrystallization from ethyl acetate

Sources & evidence

ORD record
ord-9d23b188d1cc470eb3bcb314b4823adb
Source dataset
uspto-grants-1976_06
Patent number
US03963777

Reaction notes

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