Dimethylamine → Indole, 3-((dimethylamino)methyl)-7-nitro-

HRID 641431

Reaction equation

HRID 641431 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][CH:10]=[CH:9]2)([O-:3])=[O:2].[CH3:13][NH:14][CH3:15].[CH2:16]=O.[OH-].[Na+]>O>[CH3:13][N:14]([CH3:16])[CH2:15][C:9]1[C:8]2[C:12](=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][CH:7]=2)[NH:11][CH:10]=1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 233967-Nitroindole

Product 1

HCID 15451Indole, 3-((dimethylamino)methyl)-7-nitro-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 7-nitro-1H-indole (3 g, 18.5 mmol), 40% aqueous dimethylamine (3.12 mL, 27.7 mmol) and 37% aqueous formaldehyde (1.57 mL, 19.3 mmol) was stirred for three days at ambient temperature. The reaction mixture was diluted with H2O (20 mL) followed 15% aqueous NaOH (200 mL) and extracted with CHCl3 (3×200 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo to give the title compound in sufficient purity for use in the next step. MS: m/z=181 (M+1).

Workup

  1. extractionextracted with CHCl3 (3×200 mL)
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4172bf92b7a34ba9b6fb482f83652f4e
Source dataset
uspto-grants-2010_04
Patent number
US07696192B2

Linked notes

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