HCID 68526474, compound → HCID 68526880, compound

HRID 1258545Notes

Reaction equation

HRID 1258545 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:20]#[N:21])=[C:8]([NH:10][C:11](=[O:19])[C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH:9]=1)([O-])=O.[H][H]>C1(C)C=CC=CC=1.O.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:20]#[N:21])=[C:8]([NH:10][C:11](=[O:19])[C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH:9]=1

Participants

6

Reactant 2

HCID 68526474HCID 68526474, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68526880HCID 68526880, compoundYield 75%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of N-(5-nitro-2-cyano-phenyl)-4-fluoro-benzamide (1.79 g) (Example 18) in a mixture of toluene (100 ml) and water (10 ml) was added palladium on charcoal (5%) (180 mg). The reactor was charged with hydrogen (471.72 ml, 10 bar) and the reaction mixture was heated to 80° C. for 4 hours. The reaction mixture was filtered to remove the palladium catalyst and the filtrate concentrated. The residue was purified by column chromatography on silica gel (eluent: cyclohexane/tetrahydrofuran 1:1) to give N-(5-amino-2-cyano-phenyl)-4-fluoro-benzamide (1.2 g, 75% yield). 1H-NMR (CDCl3, 400 MHz): 8.28 (s, 1H), 7.98 (m, 3H), 7.40 (d, 1H), 7.22 (t, 1H), 6.43 (m, 1H), 4.3 (s, 2H) ppm.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the palladium catalyst
  3. concentrationthe filtrate concentrated
  4. customThe residue was purified by column chromatography on silica gel (eluent: cyclohexane/tetrahydrofuran 1:1)

Sources & evidence

ORD record
ord-fd8f09411ba54eb483cbf2a0c64774f3
Source dataset
uspto-grants-2013_06
Patent number
US08466180B2

Reaction notes

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