Reaction #3709

Reaction equation

3-methoxy-4-nitrobenzoyl chloride

10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine

triethylamine

→

off-white solid

Yield 104.2%

10,11-Dihydro-10-(4-nitro-3-methoxybenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine

Yield 104.2%

Solvents

methylene chloride

Conditions

Workup

1. 1
   Otherquenched with 10 ml of 1N NaOH
2. 2
   OtherThe methylene chloride layer is evaporated
3. 3
   Filtrationthe resulting suspension filtered
4. 4
   WashThe precipitate is washed with 1N NaOH (2×5 ml), water (3×5 ml) and hexane (2×5 ml)
5. 5
   OtherThe collected solid is dried in vacuo

Procedure

To a solution of 0.55 g of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine in 8 ml of methylene chloride is added 0.55 g of triethylamine followed by 0.97 g of 3-methoxy-4-nitrobenzoyl chloride. The reaction mixture is stirred at room temperature for 2 hours and then quenched with 10 ml of 1N NaOH. The methylene chloride layer is evaporated and the resulting suspension filtered. The precipitate is washed with 1N NaOH (2×5 ml), water (3×5 ml) and hexane (2×5 ml). The collected solid is dried in vacuo to give 1.13 g of off-white solid. MS(CI): 364(M+H).

Source