Hydrochloric Acid → 1-(4-Nitrophenyl)-4-methyl-7,8-methylenedioxy-3,4-dihydro-5H-2,3-benzodiazepine

HRID 440802

Reaction equation

HRID 440802 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:16]3[CH:17]=[C:18]4[O:23][CH2:22][O:21][C:19]4=[CH:20][C:15]=3[CH2:14][C:13]([CH3:24])=[N:12][N:11]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(O)C.Cl.[BH4-].[Na+]>>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[C:16]3[CH:17]=[C:18]4[O:23][CH2:22][O:21][C:19]4=[CH:20][C:15]=3[CH2:14][CH:13]([CH3:24])[NH:12][N:11]=2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 4311764Sodium borohydrideHCID 109362004-nitrophenyl-4-methyl-7,8-methylenedioxy-5H-2,3-benzodiazepine

Product 1

HCID 103364221-(4-Nitrophenyl)-4-methyl-7,8-methylenedioxy-3,4-dihydro-5H-2,3-benzodiazepineYield 97.2%

Procedure

To a suspension of 5.0 g (15.5 mmol) of the known 1-(4-nitrophenyl)-4-methyl-7,8-methylenedioxy-5H-2,3-benzodiazepine (French patent specification No. 85,09793) in 380 ml of ethanol first 22.5 ml (0.278 mol) of concentrated hydrochloric acid were added at constant stirring whereupon a solution was formed within a few minutes, then 11.5 g (0.3 mole) of sodium borohydride were charged into the solution portionwise during 30 minutes. Stirring was continued for 15 minutes, then the orange-coloured precipitate formed was filtered and extracted on the filter with 4×30 ml of chloroform. The combined chloroform filtrate was evaporated under reduced pressure, the crystalline residue was brought to a filter with 200 ml of distilled water, then washed with 3×20 ml of distilled water and dried at 80°-100° C. to yield 4.90 g (97.2%) of the aimed product, m.p.: 162°-164° C.

Workup

  1. additionwere added
  2. customwas formed within a few minutes
  3. stirringStirring
  4. customthe orange-coloured precipitate formed
  5. filtrationwas filtered
  6. extractionextracted on the
  7. filtrationfilter with 4×30 ml of chloroform
  8. customThe combined chloroform filtrate was evaporated under reduced pressure
  9. filtrationa filter with 200 ml of distilled water
  10. washwashed with 3×20 ml of distilled water
  11. customdried at 80°-100° C.

Sources & evidence

ORD record
ord-8597df61446342a89bcb62b504c67cf2
Source dataset
uspto-grants-1996_05
Patent number
US05521174

Linked notes

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