HCID 86730355, compound → HCID 86730356, compound

HRID 1427055Notes

Reaction equation

HRID 1427055 reaction equation
C([O:8][C:9]1[CH:14]=[C:13](/[CH:15]=[CH:16]/[N+]([O-])=O)[C:12]([N+:20]([O-])=O)=[CH:11][C:10]=1[O:23][CH2:24][CH2:25][CH2:26][O:27][CH3:28])C1C=CC=CC=1>CO.[C].[Pd]>[CH3:28][O:27][CH2:26][CH2:25][CH2:24][O:23][C:10]1[CH:11]=[C:12]2[C:13]([CH:15]=[CH:16][NH:20]2)=[CH:14][C:9]=1[OH:8]

Participants

4

Reactant 1

HCID 86730355HCID 86730355, compound

Product 1

HCID 86730356HCID 86730356, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

10% Palladium-carbon (water content, 50%) (8 g) was added to a solution of (E)-1-(benzyloxy)-2-(3-methoxypropoxy)-4-nitro-5-(2-nitrovinyl)benzene described in Production Example 32-4 (19.6 g, 50.5 mmol) in methanol (300 mL) at room temperature. The liquid mixture was stirred under hydrogen atmosphere at room temperature for 6 hours. The reaction liquid was filtered through celite and then the filtrate was concentrated under vacuum. The residue was purified with silica gel column chromatography (n-heptane:ethyl acetate=2:1-1:1) to obtain the title compound (3.81 g, 34%).

Workup

  1. customThe reaction liquid
  2. filtrationwas filtered through celite
  3. concentrationthe filtrate was concentrated under vacuum
  4. customThe residue was purified with silica gel column chromatography (n-heptane:ethyl acetate=2:1-1:1)

Sources & evidence

ORD record
ord-c0ddff053fe943769db38f62a40c4fda
Source dataset
uspto-grants-2015_01
Patent number
US08933099B2

Reaction notes

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