5-fluoro-N-methyl-2-nitroaniline → 5-Fluoro-N1-methylbenzene-1,2-diamine

HRID 1048937Notes

Reaction equation

HRID 1048937 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-])=O)=[C:6]([CH:9]=1)[NH:7][CH3:8]>[Pd].CO>[F:1][C:2]1[CH:9]=[C:6]([NH:7][CH3:8])[C:5]([NH2:10])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 229057745-fluoro-N-methyl-2-nitroaniline

Product 1

HCID 184572835-Fluoro-N1-methylbenzene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To the title compound from Example 1 Step A (0.267 g, 1.57 mmol) were added palladium on carbon (0.027 g) and methanol (7.85 mL). The resulting mixture was stirred under an atmosphere of hydrogen at room temperature overnight. The mixture was then filtered through CELITE® using dichloromethane, and the filtrate was concentrated. Purification by flash chromatography (50% ethyl acetate in hexanes, then 100% ethyl acetate) provided the title compound: 1H NMR (500 MHz, CDCl3) δ 6.61 (dd, J=8.2, 5.6 Hz, 1 H), 6.36-6.30 (m, 2 H), 3.22 (br s, 3 H), 2.84 (s, 3 H).

Workup

  1. filtrationThe mixture was then filtered through CELITE®
  2. concentrationthe filtrate was concentrated
  3. customPurification by flash chromatography (50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-33b884d3682748a2a1cef0f56413be90
Source dataset
uspto-grants-2016_07
Patent number
US09382226B2

Reaction notes

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