Methanol → HCID 136487410, compound

HRID 268089Notes

Reaction equation

HRID 268089 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:19][C:18]([C:20](=[N:22][OH:23])[NH2:21])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.O.CO.CCCCCC>C(OCC)(=O)C.[Pd]>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:19][C:18]([C:20](=[N:22][OH:23])[NH2:21])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 962WaterHCID 8058HexaneHCID 54019477HCID 54019477, compound

Product 1

HCID 136487410HCID 136487410, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

A mixture of 15 g (0.048 mole) of the compound of Example V, 1 tsp. of 5% Pd/C, 50% H2O, and 135 ml of methanol was shaken under hydrogen pressure with the theoretical amount of H2 being absorbed. The catalyst was removed by filtration and the solvent removed on the Calab evaporator to give a residual solid. The solid was refluxed in 750 ml of ethyl acetate, cooled in an ice bath and the insoluble material removed by filtration. The filtrate was reduced to 300 ml volume on the Calab evaporator and then diluted with hexane. The resulting solid was filtered and air dried to yield 5.4 g (46%). An analytical sample was prepared by dissolving a sample in refluxing ethyl acetate and adding hexane to the cloud point. This procedure was repeated three times, m.p. 157°-158°.

Workup

  1. customabsorbed
  2. customThe catalyst was removed by filtration
  3. customthe solvent removed on the Calab evaporator
  4. customto give a residual solid
  5. temperaturecooled in an ice bath
  6. customthe insoluble material removed by filtration
  7. customThe filtrate was reduced to 300 ml volume on the Calab evaporator
  8. additiondiluted with hexane
  9. filtrationThe resulting solid was filtered
  10. customair dried
  11. customto yield 5.4 g (46%)
  12. customAn analytical sample was prepared
  13. dissolutionby dissolving a sample

Sources & evidence

ORD record
ord-b13328080d4e4ca69583cbbb64317292
Source dataset
uspto-grants-1976_03
Patent number
US03946049

Reaction notes

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