Sodium Hydroxide → 2-Methyl-5-nitro-1-(4-nitrophenoxycarbonyl)indole

HRID 2175386Notes

Reaction equation

HRID 2175386 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][C:7]([N+:11]([O-:13])=[O:12])=[CH:6][CH:5]=2.[OH-].[Na+].Cl[C:17]([O:19][C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=1)=[O:18]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[CH3:1][C:2]1[N:3]([C:17]([O:19][C:20]2[CH:21]=[CH:22][C:23]([N+:26]([O-:28])=[O:27])=[CH:24][CH:25]=2)=[O:18])[C:4]2[C:9]([CH:10]=1)=[CH:8][C:7]([N+:11]([O-:13])=[O:12])=[CH:6][CH:5]=2

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 821294-Nitrophenyl chloroformateHCID 2803132-Methyl-5-nitro-1H-indole

Product 1

HCID 226036172-Methyl-5-nitro-1-(4-nitrophenoxycarbonyl)indoleYield 96.8%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolvent

Procedure

2-methyl-5-nitroindole (2 g, 8.78 mmol) was dissolved into 80 ml of dichloromethane, and then sodium hydroxide (1.1 g, 26.36 mmol), tetrabutylammonium bromide (32 mg, 0.87 mmol), and 4-nitrophenyl chloroformate (1.86 g, 9.22 mmol) were sequentially added followed by stirring at room temperature for 1 hour. After filtering out the solid made in the reaction, the reaction mixture was washed with dichloromethane. The resultant liquid layer was concentrated and 2-methyl-5-nitro-1-(4-nitrophenoxycarbonyl)indole (2.9 g, 96%) was obtained as yellow solid.

Workup

  1. filtrationAfter filtering out the solid
  2. custommade in the reaction
  3. washthe reaction mixture was washed with dichloromethane
  4. concentrationThe resultant liquid layer was concentrated

Sources & evidence

ORD record
ord-8ef8932bf6d847d99f7e6b8552d67ade
Source dataset
uspto-grants-2015_06
Patent number
US09062066B2

Reaction notes

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