Ethyl Acetate → 2-(2-Amino-4-fluoro-phenylamino)-N-isopropyl-N-(4-methoxy-phenyl)-acetamide

HRID 343153Notes

Reaction equation

HRID 343153 reaction equation
C(OCC)(=O)C.[F:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][CH2:15][C:16]([N:18]([CH:27]([CH3:29])[CH3:28])[C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)=[O:17])=[C:10]([N+:30]([O-])=O)[CH:9]=1.[H][H]>[Pd].C(O)C>[NH2:30][C:10]1[CH:9]=[C:8]([F:7])[CH:13]=[CH:12][C:11]=1[NH:14][CH2:15][C:16]([N:18]([CH:27]([CH3:29])[CH3:28])[C:19]1[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=1)=[O:17]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 540942822-(4-Fluoro-2-nitrophenylamino)-N-isopropyl-N-(4-methoxy-phenyl)-acetamideHCID 178418361HCID 178418361, compound

Product 1

HCID 541782582-(2-Amino-4-fluoro-phenylamino)-N-isopropyl-N-(4-methoxy-phenyl)-acetamideYield 83.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 30 mL ethyl acetate, 175 mL ethanol, and 2.50 g of 2-(4-Fluoro-2-nitro-phenylamino)-N-isopropyl-N-(4-methoxy-phenyl)-acetamide, prepared as in Part B, (6.92 mmol) is combined with 0.25 g of palladium on carbon (10 wt %) and hydrogenated under a hydrogen balloon over 16 hrs. The reaction mixture is filtered and evaporated in vacuo to provide 1.91 g of 2-(2-Amino-4-fluoro-phenylamino)-N-isopropyl-N-(4-methoxy-phenyl)-acetamide as a solid: 1H NMR (300 MHz, CDCl3) δ7.03 (m, 2H), 6.94 (m, 2H), 6.36 (m, 3H), 4.99 (m, 1H), 4.37 (b, 3H), 3.86 (s, 3H), 3.39 (s, 2H), 1.07 (d, 6H, J=6.8); low resolution MS (FAB)m/e 332 (MH+).

Workup

  1. filtrationThe reaction mixture is filtered
  2. customevaporated in vacuo

Sources & evidence

ORD record
ord-b87eae4914044aa8ab2957578d81419d
Source dataset
uspto-grants-1999_01
Patent number
US05859007

Reaction notes

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