Formaldehyde → 3-(Dimethylaminomethyl)-7-azaindole

HRID 1600476Notes

Reaction equation

HRID 1600476 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][N:8]=2)[CH:3]=[CH:2]1.[Cl-].[CH3:11][NH2+:12][CH3:13].[CH2:14]=O>C(O)CCC>[CH3:11][N:12]([CH2:14][C:3]1[C:4]2[C:9](=[N:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1)[CH3:13]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 92221H-Pyrrolo(2,3-b)pyridineHCID 12954980Dimethylazanium;chloride

Product 1

HCID 53835493-(Dimethylaminomethyl)-7-azaindoleYield 67.1%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

7-azaindole (5.0 g, 17 mmole), dimethylammonium chloride (3.76 g), and paraformaldehyde (1.40 g) were dissolved in n-butanol (30 mL). The reaction was refluxed for 1 hour where upon cooling to room temperature fluffy white needles crystalized out. These were filtered and washed with butanol (10 mL). The solid was dried in vacuo to a white crystalline solid massing 6.1 g. A portion of this material (2.0 g) was converted to the free base by dissolving in 20 mL water. Upon the addition of ammonium hydroxide (aqueous, 30%) (2 mL) a white precipitate formed, was filtered, washed with water (5 mL), and dried in vacuo to yield 3-(N,N-dimethylaminomethyl)-1H-pyrrolo[2,3-b]pyridine (2.0 g, 27% yield). δH (300 MHz CDCl3) 2.27 (6H, s), 3.61 (2H, s), 7.09 (1H, dd, J=4.5 and 8.0), 7.28 (1H, s), 8.04 (1H, dd, J=1.2 and 8.1), 8.32 (1H, dd, J=1.2 and 4.7), ESMS 176 (MH+)

Workup

  1. temperatureThe reaction was refluxed for 1 hour where
  2. customcrystalized out
  3. filtrationThese were filtered
  4. washwashed with butanol (10 mL)
  5. customThe solid was dried in vacuo to a white crystalline solid massing 6.1 g
  6. dissolutionby dissolving in 20 mL water
  7. additionUpon the addition of ammonium hydroxide (aqueous, 30%) (2 mL) a white precipitate
  8. customformed
  9. filtrationwas filtered
  10. washwashed with water (5 mL)
  11. customdried in vacuo

Sources & evidence

ORD record
ord-b545103e7392444bbdcf401d03288566
Source dataset
uspto-grants-1999_11
Patent number
US05976497

Reaction notes

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