Nitroethane → HCID 1809354, compound

HRID 623725Notes

Reaction equation

HRID 623725 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[N+:10]([CH2:13][CH3:14])([O-:12])=[O:11].N1CCCCC1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:9]=[CH:8][C:5](/[CH:6]=[C:13](/[N+:10]([O-:12])=[O:11])\[CH3:14])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6587NitroethaneHCID 77264-ChlorobenzaldehydeHCID 8082Piperidine

Product 1

HCID 1809354HCID 1809354, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 4-chlorobenzaldehyde (28.57 g, 203 mmol), nitroethane (44.0 mL, 610 mmol) and piperidine (4.01 mL, 40.6 mmol) in toluene (200 mL) was stirred at reflux (Dean-Stark) for 6 h and the mixture was stored at room temperature overnight. The solvent was removed under reduced pressure and the product was recrystallised from absolute EtOH. The crystals were filtered off, washed with a small amount of absolute EtOH and dried to give 23.25 g of the desired product. The mother liquor was concentrated, heated, cooled. Another batch of crystals was filtered off, washed with a small amount of absolute EtOH and dried in vacuo, to afford 3.95 g of the desired product. Total yield: 27.20 g (68%).

Workup

  1. temperatureat reflux (Dean-Stark) for 6 h
  2. customThe solvent was removed under reduced pressure
  3. customthe product was recrystallised from absolute EtOH
  4. filtrationThe crystals were filtered off
  5. washwashed with a small amount of absolute EtOH
  6. customdried

Sources & evidence

ORD record
ord-a256433fda4945b493513065ac3b801e
Source dataset
uspto-grants-2016_04
Patent number
US09302988B2

Reaction notes

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