Water → HCID 59431290, compound

HRID 505930Notes

Reaction equation

HRID 505930 reaction equation
O.C(=O)([O-])[O-].[K+].[K+].Br[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11].[CH3:15][C:16]1[NH:17][C:18]2[C:23]([CH:24]=1)=[C:22]([N+:25]([O-:27])=[O:26])[CH:21]=[CH:20][CH:19]=2>C(#N)C>[N+:25]([C:22]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:23]=1[CH:24]=[C:16]([CH3:15])[N:17]2[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])([O-:27])=[O:26]

Participants

6

Reactant 4

HCID 962Water2×HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 110951501H-Indole, 2-methyl-4-nitro-

Product 1

HCID 59431290HCID 59431290, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

Water (4.5 ml), potassium carbonate (25.9 g, 187 mmol) and ethyl bromoacetate (20.8 ml, 188 mmol) were added sequentially to a suspension of 2-methyl-4-nitro-1H-indole (30 g, 170 mmol) in acetonitrile (225 ml) and the mixture heated at 60° C. for 16 hours. After allowing to cool to ambient temperature, water (225 ml) was added and the resulting mixture was broken up and then filtered. The solid was washed with water (2×75 ml), followed by IMS (2×75 ml) then dried in a vacuum oven to give (4-nitro-2-methyl-1H-indol-1-yl)-acetic acid, ethyl ester, 32.15 g (72%).

Workup

  1. temperatureto cool to ambient temperature
  2. filtrationfiltered
  3. washThe solid was washed with water (2×75 ml)
  4. customthen dried in a vacuum oven

Sources & evidence

ORD record
ord-c3e1204296334c9ca75287e0612d163f
Source dataset
uspto-grants-2010_08
Patent number
US07781598B2

Reaction notes

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