Nitroethane → 775-31-5

HRID 623745Notes

Reaction equation

HRID 623745 reaction equation
[F: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].C(OC)(OC)OC.Cl.CN.C([O-])(=O)C.[K+]>CO>[F: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

7

Reactant 5

HCID 6587NitroethaneHCID 9005Trimethyl orthoformateHCID 680234-FluorobenzaldehydeHCID 517044Potassium AcetateHCID 6364545Methylamine hydrochloride

Product 1

HCID 5371949775-31-5Yield 25%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-fluorobenzaldehyde (5.0 g, 40.32 mmol), nitro ethane (3.2 mL, 44.35 mmol), trimethyl orthoformate (9.7 mL, 88.70 mmol), methylamine HCl (2.1 g, 31.44 mmol) and potassium acetate (2.76 g, 28.22 mmol) in methanol (50 mL) was refluxed at 80° C. for 18 h. Methanol was evaporated; the residue diluted with water (100 mL), extracted with EtOAc (3×50 mL). The combined organic layer was washed with water (50 mL), brine (50 mL), dried (Na2SO4) and concentrated. The residue triturated with methanol (10 mL), filtered off and washed with cold methanol (5 mL) to afford the desired product (1.82 g, 25%) as a yellow solid.

Workup

  1. customMethanol was evaporated
  2. additionthe residue diluted with water (100 mL)
  3. extractionextracted with EtOAc (3×50 mL)
  4. washThe combined organic layer was washed with water (50 mL), brine (50 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue triturated with methanol (10 mL)
  8. filtrationfiltered off
  9. washwashed with cold methanol (5 mL)

Sources & evidence

ORD record
ord-be8bb0e882f84489b774fcdfbdec0ffb
Source dataset
uspto-grants-2016_04
Patent number
US09302988B2

Reaction notes

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