Potassium Carbonate → 2-Nitroaniline

HRID 1048982Notes

Reaction equation

HRID 1048982 reaction equation
F[C:2]1[CH:7]=[C:6](F)[C:5](F)=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].C([O-])([O-])=O.[K+].[K+].OC(C(F)(F)F)=O.FC1C=C(CN)C=[N:31]C=1>C1COCC1.CCOC(C)=O>[N+:10]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH2:31])([O-:12])=[O:11]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 750121,2,4-Trifluoro-5-nitrobenzeneHCID 86703087HCID 86703087, compound

Product 1

HCID 69462-Nitroaniline

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

2,4,5-tri-fluoronitrobenzene (2.864 g, 0.016 mol), K2CO3 (2.236 g, 0.0161 mol) and (5-fluoropyridin-3yl)methanamine TFA salt (1.02 g, 50% LC-MS) were dissolved in THF (25 mL) and stirred at room temperature for 16 hours. The reaction mixture was then diluted with EtOAc (100 mL) and washed with H2O. The organic phase was dried and concentrated under vacuum to give the ortho-substitution product, 4,5-difluoro-N-(5-fluoropyridin-3-yl) methyl)-2-nitroaniline as a yellow solid. 1H NMR (400 MHz, DMSO-d6), δ: 8.72 (br, 1H), 8.43 (s, 1H), 8.39 (s, 1H), 8.15 (dd, J=10 Hz, 8.8 Hz, 1H), 7.65 (d, J=9.2 Hz, 1H), 6.83 (dd, J=12.8 Hz, 7.8 Hz, 1H), 4.71 (s, 2H). MS (M+1): 284

Workup

  1. washwashed with H2O
  2. customThe organic phase was dried
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-38121b3fe59f4872bdeb3c41f86ff0ca
Source dataset
uspto-grants-2016_07
Patent number
US09382226B2

Reaction notes

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