Nitromethane → HCID 1080325, compound

HRID 1843919Notes

Reaction equation

HRID 1843919 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH:12]=O)=[CH:4]1)[CH3:2].[N+:14]([CH3:17])([O-:16])=[O:15].C([O-])(=O)C.[NH4+].C(OC(=O)C)C>CCCCCC>[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH:12]=[CH:17][N+:14]([O-:16])=[O:15])=[CH:4]1)[CH3:2]

Participants

6

Reactant 4

HCID 6375NitromethaneHCID 8857Ethyl AcetateHCID 517165Ammonium AcetateHCID 5990901-Ethyl-1H-indole-3-carbaldehyde

Product 1

HCID 1080325HCID 1080325, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

1-Ethyl-1H-indole-3-carbaldehyde (I-38b: 5.2 g, 29.885 mmol), nitromethane (46.81 mL, 866.66 mmol) and ammonium acetate (1.17 g, 15.241 mmol) were taken in a reaction flask. The flask was refluxed for 16 hours under nitrogen atmosphere. The reaction was monitored by TLC (25% ethylacetate in hexane). The reaction mixture was cooled to room temperature and the reaction mixture was partitioned between water and ethylacetate. The organic layer was washed with water, brine solution, dried over Na2SO4 and concentrated to afford 4.8 g of the product (75% yield).

Workup

  1. temperatureThe flask was refluxed for 16 hours under nitrogen atmosphere
  2. customthe reaction mixture was partitioned between water and ethylacetate
  3. washThe organic layer was washed with water, brine solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-dfdeeaea0a1644c797539e65a5e8fee0
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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