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

HRID 511281Notes

Reaction equation

HRID 511281 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.[CH3:17][N:18](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl>[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:18][CH3:17])=[O:8]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27374205-Fluoro-2-nitrobenzoic acidHCID 6364545Methylamine hydrochloride

Product 1

HCID 442030775-Fluoro-N-methyl-2-nitrobenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-fluoro-2-nitrobenzoic acid (0.550 g, 2.97 mmol), methylamine hydrochloride (0.241 g, 3.56 mmol), TBTU (0.954 g, 2.97 mmol), and DIPEA (1.15 g, 8.91 mmol) in DCM (10.0 mL) was stirred at rt for 30 minutes. The reaction was quenched with saturated NaHCO3 (10 mL) and extracted with DCM (15 mL). The organic layer was washed with brine (10 mL), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to yield a yellow semi-solid. 1H NMR (CDCl3, 400 MHz): δ=3.06 (d, J=5.05 Hz, 3 H), 7.20-7.26 (m, 1 H), 8.16 (dd, J=8.84, 4.55 Hz, 1 H). MS (ES+): m/z 199.05 [MH+] (TOF, polar).

Workup

  1. customThe reaction was quenched with saturated NaHCO3 (10 mL)
  2. extractionextracted with DCM (15 mL)
  3. washThe organic layer was washed with brine (10 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto yield a yellow semi-solid

Sources & evidence

ORD record
ord-e3e3725e06ee494bb6927af39b856d9d
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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