Dimethylamine → 6-Nitrogramine

HRID 1915253Notes

Reaction equation

HRID 1915253 reaction equation
[CH3:1][NH:2][CH3:3].[CH2:4]=O.[N+:6]([C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[CH:14][NH:15]2)=[CH:11][CH:10]=1)([O-:8])=[O:7].[OH-].[Na+]>C(O)(=O)C>[CH3:1][N:2]([CH3:4])[CH2:3][C:13]1[C:12]2[C:16](=[CH:17][C:9]([N+:6]([O-:8])=[O:7])=[CH:10][CH:11]=2)[NH:15][CH:14]=1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 785026-Nitro-1H-indole

Product 1

HCID 233856-NitrogramineYield 87.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of dimethylamine (25 g, 0.17 mol) and formaldehyde (14.4 mL, 0.15 mol) in acetic acid (100 mL) was stirred at 0° C. for 30 min. To this solution was added 6-nitro-1H-indole (20 g, 0.12 mol). After stirring for 3 days at room temperature, the mixture was poured into 15% aq. NaOH solution (500 mL) at 0° C. The precipitate was collected via filtration and washed with water to give dimethyl-(6-nitro-1H-indol-3-ylmethyl)-amine (23 g, 87%).

Workup

  1. filtrationThe precipitate was collected via filtration
  2. washwashed with water

Sources & evidence

ORD record
ord-ea77d2617e43465c862f35814366e2c2
Source dataset
uspto-grants-2013_12
Patent number
US08614327B2

Reaction notes

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