N-(1H-Pyrrolo[2,3-c]pyridin-5-yl)acetamide → 1H-Pyrrolo(2,3-c)pyridin-5-amine

HRID 2393443Notes

Reaction equation

HRID 2393443 reaction equation
C([NH:4][C:5]1[CH:6]=[C:7]2[CH:13]=[CH:12][NH:11][C:8]2=[CH:9][N:10]=1)(=O)C>[OH-].[K+]>[NH3:4].[NH2:4][C:5]1[CH:6]=[C:7]2[CH:13]=[CH:12][NH:11][C:8]2=[CH:9][N:10]=1

Participants

4

Reactant 1

HCID 18975304N-(1H-Pyrrolo[2,3-c]pyridin-5-yl)acetamide

Product 2

HCID 222AmmoniaHCID 189753231H-Pyrrolo(2,3-c)pyridin-5-amineYield 164.8%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

5-Acetylamino-1H-pyrrolo[2,3-c]pyridine (0.61 g, 3.5 mmol) was heated at reflux in methanolic KOH (2M, 15 mL) under nitrogen for 8 hours. The solvent was evaporated in vacuo and the residue partitioned between dichloromethane (100 mL) and water (100 mL). The two layers were separated and the aqueous phase was extracted with n-butanol (3×100 mL). The combined organics were evaporated in vacuo and the residue chromatographed on silica eluting with 5 to 10% MeOH in DCM followed by a gradient of 90:10:1 to 80:20:1, DCM:MeOH:NH3 to give the title compound (0.384 g, 83%) as a red solid. mp 183°-186° C. 1H NMR (360 MHz, d6 -DMSO) δ 4.95 (2H, br s), 6.13-6.15 (1H, m), 6.52 (1H, s), 7.34-7.37 (1H, m), 8.17 (1H, s) and 10.90 (1H, br s).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue partitioned between dichloromethane (100 mL) and water (100 mL)
  3. customThe two layers were separated
  4. extractionthe aqueous phase was extracted with n-butanol (3×100 mL)
  5. customThe combined organics were evaporated in vacuo
  6. customthe residue chromatographed on silica eluting with 5 to 10% MeOH in DCM

Sources & evidence

ORD record
ord-db3e2375e2554a99b7713d64d71dbad8
Source dataset
uspto-grants-1998_09
Patent number
US05807857

Reaction notes

Loading…