N,N,N',N'-Tetramethylmethanediamine → 4-NITROGRAMINE

HRID 551073Notes

Reaction equation

HRID 551073 reaction equation
CN([CH2:4][N:5]([CH3:7])[CH3:6])C.[N+:8]([C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[CH:13]=[CH:14][NH:15]2)([O-:10])=[O:9].[OH-].[Na+]>C(O)(=O)C>[CH3:7][N:5]([CH3:6])[CH2:4][C:13]1[C:12]2[C:16](=[CH:17][CH:18]=[CH:19][C:11]=2[N+:8]([O-:10])=[O:9])[NH:15][CH:14]=1

Participants

5

Reactant 3

HCID 5829N,N,N',N'-TetramethylmethanediamineHCID 14798Sodium HydroxideHCID 1457664-Nitro-1H-indole

Product 1

HCID 2514534-NITROGRAMINE

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
0 °C

Procedure

N,N,N′,N′-Tetramethyldiaminomethane (2.2 mL, 15.6 mol) in acetic acid (30 mL) was added dropwise over 60 min to a solution of 4-nitroindole (2.30 g, 14.2 mol) in acetic acid (30 mL). After 3.5 h, the reaction was cooled to 0° C., and 20% aqueous sodium hydroxide was added to adjust the pH to 11. The mixture was extracted with CHCl3 (3×300 mL) and the combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo to give the title compound. MS: ml/=220 (M+1).

Workup

  1. extractionThe mixture was extracted with CHCl3 (3×300 mL)
  2. dry with materialthe combined organic extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2154decbf3dc4081937419de87701fc4
Source dataset
uspto-grants-2011_05
Patent number
US07947677B2

Reaction notes

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