N-Cyclopropyl-5-fluoro-2-nitroaniline → 1-N-cyclopropyl-5-fluorobenzene-1,2-diamine

HRID 1048944Notes

Reaction equation

HRID 1048944 reaction equation
[CH:1]1([NH:4][C:5]2[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:6]=2[N+:12]([O-])=O)[CH2:3][CH2:2]1>[Pd].CO>[CH:1]1([NH:4][C:5]2[C:6]([NH2:12])=[CH:7][CH:8]=[C:9]([F:11])[CH:10]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 53621866N-Cyclopropyl-5-fluoro-2-nitroaniline

Product 1

HCID 545925541-N-cyclopropyl-5-fluorobenzene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To the title compound from Step D (1.23 g, 6.27 mmol) were added 10% palladium on carbon (0.123 g, 1.16 mmol) and methanol (31.3 mL). The resulting mixture was stirred under an atmosphere of hydrogen at room temperature overnight. The reaction mixture was then filtered through CELITE° using dichloromethane and concentrated under reduced pressure. Purification by flash chromatography on silica gel (0 to 30% ethyl acetate in hexanes) provided the title compound: 1H NMR (500 MHz, CDCl3) δ 6.76 (dd, J=10.9, 2.8 Hz, 1 H), 6.60 (dd, J=8.4, 5.6 Hz, 1 H), 6.34 (ddd, J=11.2, 8.4, 2.8 Hz, 1 H), 4.17 (br s, 1 H), 3.01 (br s, 2 H), 2.42-2.38 (m, 1 H), 0.77-0.72 (m, 2 H), 0.54-0.51 (m, 2 H).

Workup

  1. filtrationThe reaction mixture was then filtered through CELITE°
  2. concentrationconcentrated under reduced pressure
  3. customPurification by flash chromatography on silica gel (0 to 30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-af19dc86c45e4e24b64f0db39d129cbb
Source dataset
uspto-grants-2016_07
Patent number
US09382226B2

Reaction notes

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