Ethyl bromoacetate → HCID 68696643, compound

HRID 2246708Notes

Reaction equation

HRID 2246708 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.[H-].[Na+].Br[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]>CN(C)C=O>[CH2:21]([O:20][C:18](=[O:19])[CH2:17][N:3]1[C:4]2[C:9](=[CH:8][C:7]([N+:11]([O-:13])=[O:12])=[CH:6][CH:5]=2)[CH:10]=[C:2]1[CH3:1])[CH3:22]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 2803132-Methyl-5-nitro-1H-indole

Product 1

HCID 68696643HCID 68696643, compoundYield 78.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Methyl-5-nitro-1H-indole (5.3 g) was dissolved in dimethyl formamide (20 ml) and to it added sodium hydride (1.2 g) for the mixture to be stirred for 1 hour. Ethyl bromoacetate (6.8 g) was added all at once and a precipitate started to form. The mixture was quenched with 1% aqueous acetic acid and the precipitate collected by filtration and washed thoroughly with water, triturated with diethyl ether and dried under vacuum to give pure sub-title product (6.2 g).

Workup

  1. customto form
  2. customThe mixture was quenched with 1% aqueous acetic acid
  3. filtrationthe precipitate collected by filtration
  4. washwashed thoroughly with water
  5. customtriturated with diethyl ether
  6. customdried under vacuum

Sources & evidence

ORD record
ord-8f7a8be235604f2591b09ea0af7851a8
Source dataset
uspto-grants-2010_03
Patent number
US07687535B2

Reaction notes

Loading…