Hydrochloric Acid → 2-Cyclopropylamino-6-fluoro-3-nitrobenzoic acid

HRID 243107Notes

Reaction equation

HRID 243107 reaction equation
F[C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]([F:14])[C:3]=1[C:4]([OH:6])=[O:5].CCN(CC)CC.[CH:22]1([NH2:25])[CH2:24][CH2:23]1.Cl>O>[CH:22]1([NH:25][C:2]2[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]([F:14])[C:3]=2[C:4]([OH:6])=[O:5])[CH2:24][CH2:23]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 69828CyclopropylamineHCID 3026292,6-Difluoro-3-nitrobenzoic acid

Product 1

HCID 681570042-Cyclopropylamino-6-fluoro-3-nitrobenzoic acidYield 71.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2,6-difluoro-3-nitrobenzoic acid (1.0 g, 4.92 mmol) in IMS (5 mL) and water (5 mL) were added Et3N (1.23 mL, 8.86 mmol) and cyclopropylamine (360 μL, 5.17 mmol). The reaction mixture was stirred at RT for 28 h. The pH of the solution was adjusted to 1 by addition of 1M aqueous HCl. A precipitate formed and this solid was collected by filtration, washing with water to afford the title compound (841 mg, 71%) as a yellow solid. 1H NMR (CDCl3, 400 MHz): δ 8.78 (1H, s), 8.28 (1H, dd, J=9.45, 5.85 Hz), 6.49 (1H, m), 2.84 (1H, m), 0.85 (2H, m), 0.68 (2H, m)

Workup

  1. customA precipitate formed
  2. filtrationthis solid was collected by filtration
  3. washwashing with water

Sources & evidence

ORD record
ord-e396967288734772a42910052cb3d439
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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