HCID 19878623, compound → HCID 19878629, compound

HRID 1885498Notes

Reaction equation

HRID 1885498 reaction equation
[CH2:1]([O:8][C:9]([N:11]([C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][C:16]=1[OH:24])[CH2:12][CH2:13][OH:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>C(OCC)(=O)C.[Ni]>[NH2:21][C:18]1[CH:19]=[CH:20][C:15]([N:11]([C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])[CH2:12][CH2:13][OH:14])=[C:16]([OH:24])[CH:17]=1

Participants

5

Reactant 2

HCID 19878623HCID 19878623, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19878629HCID 19878629, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolvent

Procedure

0.24 mole (80 g) of 2-[N-benzyloxycarbonyl-N-(β-hydroxyethyl)amino]-5-nitrophenol in 630 ml of ethyl acetate is subjected to a hydrogen pressure of 9×105 pascals (9 bars) in an autoclave in the presence of 15 g of Raney nickel (water content 50%). After one hour at 85° C., the reaction medium is filtered while hot in order to remove the catalyst. On evaporation of the solvent under vacuum, the expected product crystallizes. After draining and drying, the product obtained is recrystallized from 96° strength alcohol It melts at 142° C.

Workup

  1. filtrationthe reaction medium is filtered while hot in order
  2. customto remove the catalyst
  3. customOn evaporation of the solvent under vacuum
  4. customthe expected product crystallizes
  5. customdrying
  6. customthe product obtained
  7. customis recrystallized from 96° strength alcohol It melts at 142° C.

Sources & evidence

ORD record
ord-23cd91a059cf4e6e817eca8206da5854
Source dataset
uspto-grants-1992_09
Patent number
US05145483

Reaction notes

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