Formaldehyde → HCID 57619349, compound

HRID 1952100Notes

Reaction equation

HRID 1952100 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 (532, 8.00 g, 0.0524 mol) in isopropyl alcohol (250.0 mL) were added dimethylamine hydrochloride (4.79 g, 0.0587 mol) and formaldehyde (1.77 g, 0.0589 mol). 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 (533, 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-ee18178ca456415f945d36be4c830ae1
Source dataset
uspto-grants-2013_03
Patent number
US08404700B2

Reaction notes

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