Formaldehyde → HCID 18946789, compound

HRID 1769211Notes

Reaction equation

HRID 1769211 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][NH:12][CH3:13].C=O>C(O)CCC>[CH3:11][N:12]([CH3:13])[C:3]1[C:4]2[C:9](=[N:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1

Participants

5

Reactant 3

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

Product 1

HCID 18946789HCID 18946789, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

To 40 ml of n-butyl alcohol was added 1.18 g of 7-azaindole, 0.88 g of dimethylamine hydrochloride and 0.33 g of paraformaldehyde, and the mixture refluxed for 30 minutes. The clear solution was then evaporated to dryness in vacuo, and 10 ml of 10% aqueous hydrochloric acid was added to the residue. The water layer was extracted with ether, and then made strongly basic with potassium carbonate. The resulting precipitate was filtered off, washed with ether and dried, yielding 1.42 g (81.1%) of 3-dimethylamino-7-azaindole, m.p. 144°-152° C.

Workup

  1. temperaturethe mixture refluxed for 30 minutes
  2. customThe clear solution was then evaporated to dryness in vacuo, and 10 ml of 10% aqueous hydrochloric acid
  3. additionwas added to the residue
  4. extractionThe water layer was extracted with ether
  5. filtrationThe resulting precipitate was filtered off
  6. washwashed with ether
  7. customdried

Sources & evidence

ORD record
ord-682775b56be642198c6b2debcc89c777
Source dataset
uspto-grants-1995_01
Patent number
US05380739

Reaction notes

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