HCID 178486886, compound → HCID 178486885, compound

HRID 478606Notes

Reaction equation

HRID 478606 reaction equation
[OH:1][C:2]1[N:11]=[C:10]([OH:12])[C:9]2[C:4](=[CH:5][C:6]([O:18][CH3:19])=[C:7]([O:16][CH3:17])[C:8]=2[N+:13]([O-])=O)[N:3]=1>[Pd].C(O)(=O)C.CO.C(Cl)Cl.[OH-].[Na+]>[NH2:13][C:8]1[C:7]([O:16][CH3:17])=[C:6]([O:18][CH3:19])[CH:5]=[C:4]2[C:9]=1[C:10]([OH:12])=[N:11][C:2]([OH:1])=[N:3]2

Participants

6

Reactant 1

HCID 178486886HCID 178486886, compound

Product 1

HCID 178486885HCID 178486885, compoundYield 73.6%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 14798Sodium HydroxideSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

A mixture of the product of step (b) (35.0 g, 0.13 mol) and 10% palladium on carbon (4.0 g) was suspended in glacial acetic acid (200 ml) and hydrogenated at 50 psi (3.4 atm) and 5° C. for 2.5 days. The reaction was then cooled, suspended in MeOH/CH2Cl2 (1/1 v/v, 1 L) and filtered. The residue was transferred to a soxhlet apparatus and continually extracted with MeOH for 3 days. Evaporation afforded a grey solid which was dissolved in 2N NaOH, filtered through a pad of silica, washing with H2O. The filtrate was then acidified with concentrated HCl. The resulting precipitate was isolated by filtration, washing sequentially with H2O and acetone, then dried in vacuo at 60° C. to give the subtitle compound as a white solid (22.7 g, 73%). Rf 0.42 (EtOAc/MeOH 95/5, v/v). MS m/z 238 (MH+).

Workup

  1. temperatureThe reaction was then cooled
  2. filtrationfiltered
  3. extractioncontinually extracted with MeOH for 3 days
  4. customEvaporation
  5. customafforded a grey solid which
  6. filtrationfiltered through a pad of silica
  7. washwashing with H2O
  8. customThe resulting precipitate was isolated by filtration
  9. washwashing sequentially with H2O and acetone
  10. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-2ad88436b726471aba1cd494d70634d1
Source dataset
uspto-grants-2003_11
Patent number
US06642242B2

Reaction notes

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