HCID 21916128, compound → HCID 20780029, compound

HRID 1349416Notes

Reaction equation

HRID 1349416 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=2[CH3:17])=[C:4]([N+:18]([O-])=O)[CH:3]=1>[Pd].C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([NH2:18])[C:5]([NH:8][C:9]2[C:10]([CH3:17])=[CH:11][C:12]([CH3:16])=[CH:13][C:14]=2[CH3:15])=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 21916128HCID 21916128, compound

Product 1

HCID 20780029HCID 20780029, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Palladium on carbon (10%) (0.54 g) was added to a solution of (4-fluoro-2-nitro-phenyl)-(2,4,6-trimethyl-phenyl)-amine (5.32 g, 19.4 mmol) in ethyl acetate (40 mL) under nitrogen at room temperature in a 500 mL round-bottomed flask. The flask was evacuated under high vacuum (<2 mm Hg) and purged with hydrogen six times at room temperature, then it was attached to a balloon filled with hydrogen. After the reaction mixture was stirred at room temperature for 4.0 h under 1 atmosphere of hydrogen, the balloon was removed and a stream of nitrogen was bubbled through the reaction mixture for 10 min. The reaction mixture was filtered through a pad of celite and solvents were removed in vacuo to afford the title compound as a red solid (4.74 g, 100% yield). The purity of this compound was determined to be 98% by LC/MS. 1H NMR (CDCl3, 300 MHz) δ 6.93 (s, 2H), 6.52 (dd, J=9.8, 2.7 Hz, 1H), 6.32 (td, J=8.6, 2.7 HZ, 1H), 6.22 (dd, J=8.7, 5.7 Hz, 1H), 2.32 (s, 3H), 2.12 (s, 6H); 13C NMR (CDCl3, 75 MHz) δ 159.8, 156.7, 138.2 (d, J=10.5 Hz), 137.6, 133.5, 132.3, 129.5, 117.3 (d, J=9.5 Hz), 105.1 (d, J=22 Hz), 102.9 (d, J=25.5 Hz), 20.8, 18.0; Mass spec.: 245.14 (MH+)

Workup

  1. customThe flask was evacuated under high vacuum (<2 mm Hg)
  2. custompurged with hydrogen six times at room temperature
  3. additionfilled with hydrogen
  4. customthe balloon was removed
  5. customa stream of nitrogen was bubbled through the reaction mixture for 10 min
  6. filtrationThe reaction mixture was filtered through a pad of celite and solvents
  7. customwere removed in vacuo

Sources & evidence

ORD record
ord-4f6cbb3a460a411e90b7f91824f86804
Source dataset
uspto-grants-2007_05
Patent number
US07211669B2

Reaction notes

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