Acetic Acid → HCID 59300340, compound

HRID 2236770Notes

Reaction equation

HRID 2236770 reaction equation
CO[N:3]=[CH:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[C:7]([O:14][Si:15]([CH:22]([CH3:24])[CH3:23])([CH:19]([CH3:21])[CH3:20])[CH:16]([CH3:18])[CH3:17])[CH:6]=1.C(=O)=O.C(O)(=O)C.[H][H]>C(O)C.O1CCCC1.[Pd]>[NH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[C:7]([O:14][Si:15]([CH:19]([CH3:21])[CH3:20])([CH:22]([CH3:24])[CH3:23])[CH:16]([CH3:17])[CH3:18])[CH:6]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 280Carbon DioxideHCID 72250843HCID 72250843, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59300340HCID 59300340, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-nitro-3-[(triisopropylsilyl)oxy]benzaldehyde O-methyloxime (3.1 g, 9.8 mmol) in ethanol (100 mL) and tetrahydrofuran (80 mL) is degassed with solid carbon dioxide, then charged with 10% palladium on carbon (200 mg) and glacial acetic acid (1.3 mL). The mixture is shaked under 45 psi hydrogen gas for 36 hours. The mixture is then filtered through a pad of diatomaceous earth, and the filtrate is concentrated under reduced pressure to give {4-(aminomethyl)-2-[(triisopropylsilyl)oxy]phenyl}amine, a golden semi-solid, as its diacetic acid salt. This material is used in the subsequent step without further purification.

Workup

  1. filtrationThe mixture is then filtered through a pad of diatomaceous earth
  2. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-a5cc77a72f7046879d7a03cc2ab01c8d
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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