Formaldehyde → 3-(Dimethylaminomethyl)-7-azaindole

HRID 726670Notes

Reaction equation

HRID 726670 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.Cl.[CH3:11][NH:12][CH3:13].[CH2:14]=O>C(O)CCC>[CH3:11][N:12]([CH3:14])[CH2:13][C:3]1[C:4]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[NH:1][CH:2]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 92221H-Pyrrolo(2,3-b)pyridineHCID 10473Dimethylamine, hydrochloride

Product 1

HCID 53835493-(Dimethylaminomethyl)-7-azaindoleYield 50%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 1H-pyrrolo[2,3-b]pyridine (59 g; 0.5 mol), dimethylamine hydrochloride (44.83 g; 0.55 mol) and paraformaldehyde (16.5 g; 0.55 mol) in n-butanol (700 mL) was heated at reflux for 20 minutes. The mixture was cooled to ambient temperature. The precipitated solid was collected by filtration and dried. The solid was then dissolved in water (800 mL), a few drops of HCl was added for complete solution. The aqueous solution was washed with diethyl ether. Solid potassium carbonate was then added to the aqueous phase until basic. The precipitated solid was collected, washed with water and dried to give 43.5 g (50% yield) of the title compound as an off-white solid, m.p. 161°-162° C. Anal. Calcd. for C10H13N3 : C, 68.54; H, 7.48; N, 23.95. Found: C, 68.28; H, 7.75; N, 23.99. Mass spectrum (DEI; M+) m/z 175. 1H-NMR (DMSO-d6 ; 400 MHz) δ 12.45 (br s, 1H), 8.14 (dd, 1H), 7.97 (dd, 1H), 7.32 (s, 1H), 7.01 (q, 1H), 3.51 (s, 2H), and 2.12 ppm (s, 6H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 20 minutes
  3. filtrationThe precipitated solid was collected by filtration
  4. customdried
  5. dissolutionThe solid was then dissolved in water (800 mL)
  6. additiona few drops of HCl was added for complete solution
  7. washThe aqueous solution was washed with diethyl ether
  8. additionSolid potassium carbonate was then added to the aqueous phase until basic
  9. customThe precipitated solid was collected
  10. washwashed with water
  11. customdried

Sources & evidence

ORD record
ord-14fa79594baf487ebaa56e5b994c3da3
Source dataset
uspto-grants-1998_01
Patent number
US05710164

Reaction notes

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