HCID 10730528, compound → HCID 10705025, compound

HRID 395737Notes

Reaction equation

HRID 395737 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=1)[C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-])=O)=[O:7])#[N:2]>[Pd].C(OCC)(=O)C>[C:1]([C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=1)[C:6]([NH:8][C:9]1[C:10]([NH2:15])=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:7])#[N:2]

Participants

4

Reactant 1

HCID 10730528HCID 10730528, compound

Product 1

HCID 10705025HCID 10705025, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-(3-cyanobenzoyl)-2-nitroaniline (1.0 g, 3.7 mmol), 10% palladium-on-carbon, and ethyl acetate (250 mL) was hydrogenated at one atmospheric pressure for 30 min. The mixture was filtered through diatomaceous earth and concentrated in vauco. Chromatography (silica gel, 50% ethyl acetate/50% hexanes) of the residue yielded 630 mg (72%) of the title compound as a yellow solid, mp 197-200° C.

Workup

  1. filtrationThe mixture was filtered through diatomaceous earth
  2. concentrationconcentrated in vauco

Sources & evidence

ORD record
ord-7eb7b6d4f2dc4b30a7cded75f361976e
Source dataset
uspto-grants-2003_08
Patent number
US06605626B2

Reaction notes

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