Acetic Anhydride → HCID 15299309, compound

HRID 1292028Notes

Reaction equation

HRID 1292028 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][CH:13]([CH3:24])[NH:12][N:11]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:25](OC(=O)C)(=[O:27])[CH3:26]>>[C:25]([N:12]1[C:13]([CH3:24])=[CH:14][C:15]2[CH:20]=[C:19]3[O:21][CH2:22][O:23][C:18]3=[CH:17][C:16]=2[C:10]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)=[N:11]1)(=[O:27])[CH3:26]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 103364221-(4-Nitrophenyl)-4-methyl-7,8-methylenedioxy-3,4-dihydro-5H-2,3-benzodiazepine

Product 1

HCID 15299309HCID 15299309, compoundYield 70%

Procedure

A suspension of 1.0 g (3.1 mmol) of 5-(4-nitrophenyl)-8-methyl-9H-7H-1,3-dioxolo[4,5-h][2,3]-benzodiazepine is heated in 10 ml of acetic anhydride for 7 hours to 130°-140° C. The solution is poured on ice, and the precipitate is suctioned off. 0.99 g (87% of theory) of a yellow powder is obtained. After combining the corresponding fractions and concentration by evaporation, flash chromatography of this crude product on silica gel 60 with benzene/ethyl acetate (4:1) as a mobile solvent yields 0.78 g (70% of theory) of 7-acetyl-5-(4-nitrophenyl)-8-methyl-7H-1,3-dioxolo[4,5-h][2,3]-benzodiazepine as a solid with a melting point of 200°-202° C. A sample is recrystallized from ethanol and then has a melting point of 205°-207° C. (minor decomposition).

Workup

  1. additionThe solution is poured on ice
  2. custom0.99 g (87% of theory) of a yellow powder is obtained
  3. concentrationthe corresponding fractions and concentration
  4. customby evaporation, flash chromatography of this crude product on silica gel 60 with benzene/ethyl acetate (4:1) as a mobile solvent

Sources & evidence

ORD record
ord-a9f61a7b74a5494bba88e8fef77ee53d
Source dataset
uspto-grants-1998_05
Patent number
US05756495

Reaction notes

Loading…