Ammonium Chloride → Ethyl 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylate

HRID 1693357Notes

Reaction equation

HRID 1693357 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[C:5](=O)[CH2:6][C:7]1[C:12]([N+:13]([O-])=O)=[CH:11][N:10]=[C:9]([Cl:16])[CH:8]=1)[CH3:2].[Cl-].[NH4+]>C(O)C.C1COCC1.[Fe]>[CH2:1]([O:3][C:4]([C:5]1[NH:13][C:12]2=[CH:11][N:10]=[C:9]([Cl:16])[CH:8]=[C:7]2[CH:6]=1)=[O:18])[CH3:2]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 53472030Ethyl 3-(2-chloro-5-nitropyridin-4-yl)-2-oxopropanoate

Product 1

HCID 44630703Ethyl 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylate

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-(2-Chloro-5-nitropyridin-4-yl)-2-oxopropionic acid ethyl ester (Preparation 16, 3.0 g, 11.0 mmol) was dissolved in ethanol (100 mL) and THF (50 mL). Iron powder (3.7 g, 66.0 mmol) and saturated ammonium chloride solution (50 mL) were added and the mixture heated under reflux for 2 h. The mixture was cooled, filtered through celite and washed several times with ethyl acetate. The organic layers were combined, washed with brine (100 mL), dried (MgSO4) and concentrated in vacuo to give the title compound as a brown solid. δH (CD3OD): 1.42 (3H, t), 4.44 (2H, q), 7.15 (1H, s), 7.70 (1H, s), 8.59 (1H, s); m/z (ES+)=225 [M+H]+.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 2 h
  3. temperatureThe mixture was cooled
  4. filtrationfiltered through celite
  5. washwashed several times with ethyl acetate
  6. washwashed with brine (100 mL)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3e42231fdbea4915bca15df87b62da2b
Source dataset
uspto-grants-2012_04
Patent number
US08158622B2

Reaction notes

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