Ethanol → 2,3-dimethyl-1H-pyrrolo[2,3-b]pyridin-5-amine

HRID 2196719Notes

Reaction equation

HRID 2196719 reaction equation
[CH3:1][C:2]1[NH:13][C:5]2=[N:6][CH:7]=[C:8]([N+:10]([O-])=O)[CH:9]=[C:4]2[C:3]=1[CH3:14].[Cl-].[NH4+].C(O)C>[Fe].O>[CH3:1][C:2]1[NH:13][C:5]2=[N:6][CH:7]=[C:8]([NH2:10])[CH:9]=[C:4]2[C:3]=1[CH3:14]

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 671560892,3-dimethyl-5-nitro-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 671560582,3-dimethyl-1H-pyrrolo[2,3-b]pyridin-5-amineYield 100%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

2,3-Dimethyl-5-nitro-1H-pyrrolo[2,3-b]pyridine (0.11 g, 0.596 mmol), iron (0.40 g, 7.16 mmol) and ammonium chloride (0.13 g, 2.39 mmol) were combined with ethanol (2.8 mL) and water (0.65 mL) in a microwave vessel and heated in a microwave reactor to 110° C. for 15 minutes. The reaction mixture was filtered, saturated aqueous sodium bicarbonate was added, and the layers were separated. The aqueous layer was extracted once with ethyl acetate. The organic layers were dried with sodium sulfate, filtered and concentrated in vacuo to afford 2,3-dimethyl-1H-pyrrolo[2,3-b]pyridin-5-amine (0.096 g, 100%), which was carried to the next step without further purification.

Workup

  1. filtrationThe reaction mixture was filtered
  2. additionsaturated aqueous sodium bicarbonate was added
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted once with ethyl acetate
  5. dry with materialThe organic layers were dried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-babc7a234d8f4e898c861bdcc819453c
Source dataset
uspto-grants-2012_12
Patent number
US08338452B2

Reaction notes

Loading…