Nitromethane → HCID 66803492, compound

HRID 1843990Notes

Reaction equation

HRID 1843990 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([CH:17]=O)=[CH:9]2)=[CH:5][CH:4]=1.[N+:21]([CH3:24])([O-:23])=[O:22].C([O-])(=O)C.[NH4+]>>[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](/[CH:17]=[CH:24]\[N+:21]([O-:23])=[O:22])=[CH:9]2)=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 20109664HCID 20109664, compound

Product 1

HCID 66803492HCID 66803492, compoundYield 78.1%

Procedure

1-(4-Methoxybenzyl)-1H-indole-3-carbaldehyde (I-61a: 22 g, 83.01 mmol) was refluxed overnight with nitromethane (146 g, 2407 mmol) and ammonium acetate (3.26 g, 42.33 mmol) to afford the crude product. The reaction mass was cooled to room temperature and filtered. The solid collected was washed with water and dried under reduced pressure to afford 20 g of the product (76% yield).

Workup

  1. customto afford the crude product
  2. filtrationfiltered
  3. customThe solid collected
  4. washwas washed with water
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-8e935ed164be4655a06baf18e4780aa3
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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