Hydrochloric Acid → 1H-Pyrrolo[2,3-b]pyridine-3-carbonitrile, 1-(1,1-dimethylethyl)-5-nitro-

HRID 217954Notes

Reaction equation

HRID 217954 reaction equation
[NH2:1][C:2]1[N:6]([C:7]([CH3:10])([CH3:9])[CH3:8])[CH:5]=[C:4]([C:11]#[N:12])[CH:3]=1.[N+:13]([CH:16]([CH:19]=O)[CH:17]=O)([O-:15])=[O:14].[Na].Cl>C(O)CC>[C:7]([N:6]1[C:2]2=[N:1][CH:17]=[C:16]([N+:13]([O-:15])=[O:14])[CH:19]=[C:3]2[C:4]([C:11]#[N:12])=[CH:5]1)([CH3:8])([CH3:9])[CH3:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 103132615-amino-1-tert-butyl-1H-pyrrole-3-carbonitrileHCID 24193465CID 24193465

Product 1

HCID 669245201H-Pyrrolo[2,3-b]pyridine-3-carbonitrile, 1-(1,1-dimethylethyl)-5-nitro-Yield 81.7%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

To a solution of 5.85 g (35.8 mmol) of 5-amino-1-tert-butyl-1H-pyrrole-3-carbonitrile, being prepared as disclosed in Org. Proc. Res. Dev., 7(2), 209-213, 2003, in 120 mL of n-propanol, it was added sodium nitromalonaldehyde (6.02 g, 43.0 mmol) portionwise under stirring at room temperature. The resulting mixture was treated dropwise with 37% hydrochloric acid (4.6 mL, 55.2 mmol) and heated at 100° C. for 2 hours. The reaction mass was concentrated under vacuum to ⅓ of the initial volume and kept at 4° C. for 18 hours. The precipitate was filtered off, washed thoroughly with 15% aqueous ethanol (35 mL), water (5 mL) and finally dried to afford 7.14 g of the title compound as a light brown solid.

Workup

  1. temperatureheated at 100° C. for 2 hours
  2. concentrationThe reaction mass was concentrated under vacuum
  3. filtrationThe precipitate was filtered off
  4. washwashed thoroughly with 15% aqueous ethanol (35 mL), water (5 mL)
  5. customfinally dried

Sources & evidence

ORD record
ord-b15f3fbd721f4e748c4e85f3bd02b160
Source dataset
uspto-grants-2012_06
Patent number
US08198298B2

Reaction notes

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