1,2-Dichloroethane → 4-fluoro-3-nitro-N-methylbenzamide

HRID 722418Notes

Reaction equation

HRID 722418 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].C(Cl)CCl.[CH3:18][NH2:19]>ClCCl.C(OCC)(=O)C>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:19][CH3:18])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 6329MethylamineHCID 679874-Fluoro-3-nitrobenzoic acid

Product 1

HCID 218841864-fluoro-3-nitro-N-methylbenzamideYield 91.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Fluoro-3-nitrobenzoic acid (3.00 g, 16.2 mmoles) was dissolved in dichloromethane (100 mL) and cooled in an ice bath to 0–5° C. EDC (3.73 g, 19.5 mmoles) was added followed by dropwise addition of methylamine solution (8.1 mL, 16.2 mmoles, 2.0 M solution in THF). The mixture was allowed to slowly warm to room temperature and stirred for 2 h. The mixture was then diluted with ethyl acetate and washed successively with 1 M HCl, saturated aqueous NaHCO3 and brine. The organic extracts were dried over MgSO4, filtered and concentrated in vacuo to leave 4-fluoro-3-nitro-N-methylbenzamide as a yellow solid (2.94 g, 91%) which was used directly in the next step.

Workup

  1. temperaturecooled in an ice bath to 0–5° C
  2. washwashed successively with 1 M HCl, saturated aqueous NaHCO3 and brine
  3. dry with materialThe organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-833b19de1cad41b1935afcaaf14b5197
Source dataset
uspto-grants-2006_11
Patent number
US07138420B2

Reaction notes

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