Sodium Hydroxide → 5-(4-Nitrophenyl)-9H-[1,3-]dioxolo[4,5-h][2,3]-benzodiazepine-8-carboxylic acid

HRID 1359564Notes

Reaction equation

HRID 1359564 reaction equation
[OH-:1].[Na+].[CH:3]([C:5]1[CH2:11][C:10]2[CH:12]=[C:13]3[O:18][CH2:17][O:16][C:14]3=[CH:15][C:9]=2[C:8]([C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=2)=[N:7][N:6]=1)=[O:4]>O.O1CCOCC1.[N+]([O-])([O-])=O.[Ag+]>[N+:25]([C:22]1[CH:21]=[CH:20][C:19]([C:8]2[C:9]3[CH:15]=[C:14]4[O:16][CH2:17][O:18][C:13]4=[CH:12][C:10]=3[CH2:11][C:5]([C:3]([OH:1])=[O:4])=[N:6][N:7]=2)=[CH:24][CH:23]=1)([O-:27])=[O:26]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 108930778-formyl-5-(4-nitrophenyl)-9H-1,3-dioxolo[4,5-h][2,3]benzodiazepine

Product 1

HCID 181831855-(4-Nitrophenyl)-9H-[1,3-]dioxolo[4,5-h][2,3]-benzodiazepine-8-carboxylic acid

Reagents, catalysts & solvents 3

HCID 24470Silver NitrateCatalystHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
25 °C

Procedure

42 ml of a 4% NaOH solution is added to a solution of 3.0 g of AgNO3 in water (50 ml). The solution of 3.0 g of 8-formyl-5-(4-nitrophenyl)-9H-1,3-dioxolo[4,5-h-][2,3]-benzodiazepine in 120 ml of dioxane is slowly added to the heterogeneous mixture, and the reaction mixture is stirred for 30 minutes at 25° C. After activated carbon is added, it is filtered, the filtrate is concentrated by evaporation in a vacuum at 50-60° C., the suspension that is produced is diluted with 30 ml of water and cooled. After standing overnight, it is filtered off, the precipitate is washed with 2×10 ml of ice water, and 1.94 g of sodium salt, which is dissolved in 60 ml of hot water and, after cooling, acidified with 1 ml of acetic acid, is obtained. After filtration and washing with water, 1.66 g (53%) of product with a melting point of 196-198° C. (decomposition) is obtained.

Workup

  1. additionAfter activated carbon is added
  2. filtrationit is filtered
  3. concentrationthe filtrate is concentrated by evaporation in a vacuum at 50-60° C.
  4. customthe suspension that is produced
  5. temperaturecooled
  6. waitAfter standing overnight
  7. filtrationit is filtered off
  8. washthe precipitate is washed with 2×10 ml of ice water, and 1.94 g of sodium salt, which
  9. dissolutionis dissolved in 60 ml of hot water
  10. temperatureafter cooling
  11. customis obtained
  12. filtrationAfter filtration
  13. washwashing with water, 1.66 g (53%) of product with a melting point of 196-198° C. (decomposition)
  14. customis obtained

Sources & evidence

ORD record
ord-dcad28b1421b4093973a07a59b868895
Source dataset
uspto-grants-2003_07
Patent number
US06600036B2

Reaction notes

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