Ammonium Chloride → ethyl 1H-pyrrolo[2,3-c]pyridine-2-carboxylate

HRID 1693353Notes

Reaction equation

HRID 1693353 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[C:5](=O)[CH2:6][C:7]1[CH:12]=[CH:11][N:10]=[CH:9][C:8]=1[N+:13]([O-])=O)[CH3:2].[Cl-].[NH4+]>C(O)C.C1COCC1.[Fe]>[CH2:1]([O:3][C:4]([C:5]1[NH:13][C:8]2=[CH:9][N:10]=[CH:11][CH:12]=[C:7]2[CH:6]=1)=[O:17])[CH3:2]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 23269548Ethyl 3-(3-nitropyridin-4-yl)-2-oxopropanoate

Product 1

HCID 21819001ethyl 1H-pyrrolo[2,3-c]pyridine-2-carboxylate

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(3-nitropyridin-4-yl)-2-oxopropionic acid ethyl ester (Preparation 13, 500 mg, 2.1 mmol) in ethanol (20 mL) and THF (10 mL) was added saturated ammonium chloride solution (10 mL) and iron powder (700 mg, 12.6 mmol). The reaction was heated under reflux for 1 h, then filtered through celite and washed through with hot ethyl acetate (3×30 mL). The combined organic fractions were washed with brine (20 mL), dried (MgSO4) and concentrated in vacuo to give the title compound as a brown solid. δH (CD3OD): 1.44 (3H, t), 4.43 (2H, q), 7.21 (1H, s), 7.69 (1H, d), 8.12 (1H, d), 8.80 (1H, s).

Workup

  1. temperatureThe reaction was heated
  2. temperatureunder reflux for 1 h
  3. filtrationfiltered through celite
  4. washwashed through with hot ethyl acetate (3×30 mL)
  5. washThe combined organic fractions were washed with brine (20 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9172b1f508d9421c88b8d20d627fea1f
Source dataset
uspto-grants-2012_04
Patent number
US08158622B2

Reaction notes

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