Acetic Acid → 3-(2-DIMETHYLAMINOETHYL)-5-NITROINDOLE

HRID 1371900Notes

Reaction equation

HRID 1371900 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2)([O-:3])=[O:2].[C:13](O)(=O)[CH3:14].[CH3:17][N+:18](C)=[CH2:19].[I-]>C1(C)C=CC=CC=1>[CH3:17][N:18]([CH3:19])[CH2:13][CH2:14][C:7]1[C:6]2[C:10](=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[NH:9][CH:8]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 225235-NitroindoleHCID 2724133Dimethyl(methylene)ammounium iodide

Product 1

HCID 9499653-(2-DIMETHYLAMINOETHYL)-5-NITROINDOLE

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Warm mixture of 5-nitroindole (10 g, 62 mmol) and 200 mL glacial acetic acid to 70° C. and treat with Eschenmoser's salt (12 g, 65 mmol). Concentrate after 1 hour the reaction under vacuum to dryness. Mix the residue with 200 mL toluene, reconcentrate to dryness then partition between 200 mL concentrated ammonium hydroxide and 200 mL EtOAc. When all solids dissolved, Separate the layers and extract the aqueous layer 200 mL EtOAc. Dry the combined organic layer over MgSO4 and concentrate to give N,N-dimethyl-5-nitrotryptamine as a solid.

Workup

  1. temperatureWarm
  2. concentrationConcentrate after 1 hour
  3. customthe reaction under vacuum to dryness
  4. customthen partition between 200 mL concentrated ammonium hydroxide and 200 mL EtOAc
  5. dissolutionWhen all solids dissolved
  6. customSeparate the layers
  7. extractionextract the aqueous layer 200 mL EtOAc
  8. dry with materialDry the combined organic layer over MgSO4
  9. concentrationconcentrate

Sources & evidence

ORD record
ord-ae5cabfc25044bc1aa880160e9b87ef0
Source dataset
uspto-grants-2007_01
Patent number
US07157488B2

Reaction notes

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