Ethanol → HCID 10499221, compound

HRID 2228548Notes

Reaction equation

HRID 2228548 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][CH:28]=1)[C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][Si:16]([CH3:22])([CH3:21])[C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:11][C:10]=1[N+:23]([O-])=O)=[O:7])#[N:2].CCO>[Pd].C1COCC1>[C:1]([C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][CH:28]=1)[C:6]([NH:8][C:9]1[C:10]([NH2:23])=[CH:11][C:12]([O:15][Si:16]([CH3:21])([CH3:22])[C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:13][CH:14]=1)=[O:7])#[N:2]

Participants

5

Reactant 2

HCID 702EthanolHCID 10524870HCID 10524870, compound

Product 1

HCID 10499221HCID 10499221, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of N-(3-cyanobenzoyl)-2-nitro-4-(dimethyl-t-butylsiloxy)aniline (5.00 g, 12.6 mmol), 10% Pd/C (2.5 g), EtOH (160 mL), and THF (160 mL) was hydrogenated at 1 atm for 12 h. The reaction was filtered through diatomaceous earth with hot methanolic washes. The filtrate was concentrated and chromatographed (20% EtOAc/hexanes to 30% EtOAc/hexanes) to give the title compound as a solid (2.72 g, 59%).

Workup

  1. filtrationThe reaction was filtered through diatomaceous earth with hot methanolic washes
  2. concentrationThe filtrate was concentrated
  3. customchromatographed (20% EtOAc/hexanes to 30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-eba4224f2b3a4017b4eb2d25da636d00
Source dataset
uspto-grants-2002_07
Patent number
US06417200B1

Reaction notes

Loading…