Triethylamine → 5-Fluoro-N-methyl-2-nitrobenzamide

HRID 1887686Notes

Reaction equation

HRID 1887686 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7](O)=[O:8].Cl.CN.C[CH2:18][N:19]=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([NH:19][CH3:18])=[O:8]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 27374205-Fluoro-2-nitrobenzoic acidHCID 6364545Methylamine hydrochloride

Product 1

HCID 442030775-Fluoro-N-methyl-2-nitrobenzamideYield 90%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-fluoro-2-nitrobenzoic acid (4.775 g, 25.8 mmol), methylamine hydrochloride (2.626 g, 38.9 mmol), EDCI (5.982 g, 31.2 mmol), HOBt (4.227 g, 31.3 mmol) and triethylamine (7.2 mL, 51.65 mmol) in DMF (50 mL) was stirred at room temperature for 24 h. It was diluted with ethyl acetate and washed with saturated sodium bicarbonate, brine and dried over magnesium sulfate. The solvent was removed and the residue was purified by silica gel chromatography (combiflash-companion; ethyl acetate/hexanes gradient) to give the title compound as a yellow solid (yield: 90%).

Workup

  1. washwashed with saturated sodium bicarbonate, brine
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was removed
  4. customthe residue was purified by silica gel chromatography (combiflash-companion; ethyl acetate/hexanes gradient)

Sources & evidence

ORD record
ord-31fe7eb1ca1d49fdba29f3ea71d06dab
Source dataset
uspto-grants-2013_08
Patent number
US08501763B2

Reaction notes

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