Formaldehyde → HCID 57619349, compound

HRID 509986Notes

Reaction equation

HRID 509986 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.Cl.[CH3:12][NH:13][CH3:14].[CH2:15]=O>C(O)(C)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([CH2:12][N:13]([CH3:15])[CH3:14])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 242292135-Chloro-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 57619349HCID 57619349, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To 5-chloro-1H-pyrrolo[2,3-b]pyridine (1, 8.00 g, 0.0524 mol) in 250 mL of isopropyl alcohol, dimethylamine hydrochloride (4.79 g, 0.0587 mol) and formaldehyde (1.77 g, 0.0589 mol) were added. The reaction was stirred at room temperature overnight, followed by refluxing for 4 hours. The reaction was concentrated, poured into water, and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated to give crude compound (140, 10.0 g, 91%), that was used directly in the next step.

Workup

  1. temperatureby refluxing for 4 hours
  2. concentrationThe reaction was concentrated
  3. additionpoured into water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-37b0d657a5e04be984e07fd58a721b9f
Source dataset
uspto-grants-2015_08
Patent number
US09096593B2

Reaction notes

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