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

HRID 1658443Notes

Reaction equation

HRID 1658443 reaction equation
[CH2:1]([N:4]1[C:10]2[CH:11]=[CH:12][C:13]([Cl:15])=[CH:14][C:9]=2[C:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[F:22])=[N:7][CH2:6][C:5]1=[O:23])[CH:2]=[CH2:3].[Mn]([O-])(=O)(=O)=[O:25].[K+].[OH2:30]>N1C=CC=CC=1>[Cl:15][C:13]1[CH:12]=[CH:11][C:10]2[N:4]([CH2:1][CH:2]([OH:25])[CH2:3][OH:30])[C:5](=[O:23])[CH2:6][N:7]=[C:8]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[F:22])[C:9]=2[CH:14]=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 1049PyridineSolvent

Procedure

33.0 g of 1-allyl-7-chloro-5-(2-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one are dissolved in 200 ml of pyridine. 16 g of potassium permanganate in 300 ml of water are added dropwise within 20 minutes at room temperature to the well-stirred solution. After the potassium permanganate addition, the mixture is extensively concentrated on a rotary evaporator. The residue is briefly boiled out with ethyl acetate and filtered off under vacuum. The ethyl acetate filtrate is extracted with water, dried over magnesium sulfate, filtered and concentrated. The residue is dissolved in a small amount of ethyl acetate and seeded. By recrystallization of the first crystals there is obtained 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. concentrationthe mixture is extensively concentrated on a rotary evaporator
  2. filtrationfiltered off under vacuum
  3. extractionThe ethyl acetate filtrate is extracted with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe residue is dissolved in a small amount of ethyl acetate
  8. customBy recrystallization of the first crystals

Sources & evidence

ORD record
ord-6180ac3ffa97489fb6e493db3853ef02
Source dataset
uspto-grants-1976_06
Patent number
US03963777

Reaction notes

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