Nitromethane → HCID 66692011, compound

HRID 911214Notes

Reaction equation

HRID 911214 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=O.[N+:12]([CH3:15])([O-:14])=[O:13].C([O-])(=O)C.[NH4+]>C(O)(=O)C>[F:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=[CH:15][N+:12]([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 27348722-Fluoro-5-methoxybenzaldehyde

Product 1

HCID 66692011HCID 66692011, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Heat 2-fluoro-5-methoxybenzaldehyde (15 g, 97.4 mmol) with nitromethane (32 mL, 584 mmol) and ammonium acetate (30 g, 390 mmol) in acetic acid (136 mL) under reflux for 30 min. Evaporate the solvent and dissolve the residue in ether. Wash the organic fraction with water, saturated aqueous NaHCO3 and evaporate to give the desired intermediate (18.7 g, 97%). GC-MS m/z: 197 (M)+.

Workup

  1. temperatureunder reflux for 30 min
  2. customEvaporate the solvent
  3. dissolutiondissolve the residue in ether
  4. washWash the organic fraction with water, saturated aqueous NaHCO3
  5. customevaporate

Sources & evidence

ORD record
ord-fe66cb362fad4ef69d6b956909449f6e
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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