HCID 18433373, compound → HCID 53843249, compound

HRID 2305627Notes

Reaction equation

HRID 2305627 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:18]=[C:19]([O:24][CH3:25])[C:20]=1[N+:21]([O-])=O)[O:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])C1C=CC=CC=1>[Pd].C(O)C>[NH:21]([C:25]1[O:24][C:19]2[CH:18]=[C:11]([O:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])[CH:10]=[C:9]([O:8][CH3:1])[C:20]=2[N:21]=1)[C:20]1[CH:19]=[CH:18][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 1

HCID 18433373HCID 18433373, compound

Product 1

HCID 53843249HCID 53843249, compoundYield 158.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of methyl 3-benzyloxy-5-methoxy4-nitrophenoxyacetate(1 g), ethanol(30 mL) and 10% palladium on carbon catalyst(0.2 g) was stirred stirred under an atmosphere of hydrogen for 18 h. The mixture was filtered and the filtrate treated with phenylisothiocyanate(0.35 mL) followed by yellow mercuric oxide(0.85 g). The mixture was stirred at reflux for 4 h, then filtered and the filtrate was evaporated to dryness. The residue was purified by flash chromatography eluting with increasingly polar mixtures of ethyl acetate and hexane to give the product (0.75 g),[m/e329MH+].

Workup

  1. stirringstirred under an atmosphere of hydrogen for 18 h
  2. filtrationThe mixture was filtered
  3. additionthe filtrate treated with phenylisothiocyanate(0.35 mL)
  4. stirringThe mixture was stirred
  5. temperatureat reflux for 4 h
  6. filtrationfiltered
  7. customthe filtrate was evaporated to dryness
  8. customThe residue was purified by flash chromatography
  9. washeluting
  10. temperaturewith increasingly polar mixtures of ethyl acetate and hexane

Sources & evidence

ORD record
ord-4867985c2547429a91ef261a377f74e7
Source dataset
uspto-grants-2002_08
Patent number
US06441012B1

Reaction notes

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