HCID 18461402, compound → HCID 18461398, compound

HRID 2303911Notes

Reaction equation

HRID 2303911 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[C:7]([O:9][C:10]2[C:15]([F:16])=[C:14]([F:17])[C:13]([F:18])=[C:12]([F:19])[C:11]=2[F:20])[CH:6]=[CH:5][C:4]=1[N+:21]([O-])=O>[Pd].CO>[NH2:21][C:4]1[CH:5]=[CH:6][C:7]([O:9][C:10]2[C:15]([F:16])=[C:14]([F:17])[C:13]([F:18])=[C:12]([F:19])[C:11]=2[F:20])=[CH:8][C:3]=1[NH:2][CH3:1]

Participants

4

Reactant 1

HCID 18461402HCID 18461402, compound

Product 1

HCID 18461398HCID 18461398, compoundYield 77.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of N-methyl-N-[2-nitro-5-(pentafluorophenoxy)phenyl]amine (2.10 g), palladium on carbon (10%, 0.23 g) and methanol (300 ml) was stirred under a hydrogen atmosphere at ambient temperature for 4 hours. The catalyst was removed by filtration and the filtrate was concentrated. The residue was purified by chromatography on a silica gel column using n-hexane/ethyl acetate=3/1 as the eluant to give N-[2-amino-5-(pentafluorophenoxy)phenyl]-N-methylamine (1.48 g), of which Rf was 0.26 in thin layer chromatography on a silica gel plate using n-hexane/ethyl acetate=4/1. A mixture of this product, glycolic acid (0.76 g), 4N hydrochloric acid (25 ml) and dioxane (25 ml) was heated at reflux for 16 hours. The reaction mixture was concentrated and water was added to the residue. The mixture was neutralized with sodium bicarbonate and extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate and concentrated. The residue was purified by chromatography on a silica gel column using ethyl acetate/methanol=20/1 as the eluant. The product was crystallized from n-hexane under irradiation of ultrasonic wave. The crystals were collected by filtration and washed with n-hexane to give the title compound (1.17 g).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-a8e01dacc19348cfba75d43d80e3f437
Source dataset
uspto-grants-2002_08
Patent number
US06432993B1

Reaction notes

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