Ethanol → 1,2,3,4-Tetrahydro-4-hydroxy-1-naphthylurea

HRID 372390Notes

Reaction equation

HRID 372390 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]([NH:12][C:13]([NH2:15])=[O:14])[CH2:4][CH2:3]1.C(O)C.[BH4-].[Na+]>O>[OH:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]([NH:12][C:13]([NH2:15])=[O:14])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 702EthanolHCID 3628438Urea, (1,2,3,4-tetrahydro-4-oxo-1-naphthalenyl)-HCID 4311764Sodium borohydride

Product 1

HCID 42945181,2,3,4-Tetrahydro-4-hydroxy-1-naphthylurea

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 4.6 g. of 1,2,3,4-tetrahydro-4-oxo-1-naphthylurea in 230 ml. of ethanol 0.85 g. of sodium borohydride is added. The reaction mixture is stirred for about 5 hours and after standing overnight 50 ml. water is added while stirring. The mixture is then evaporated in vacuo to remove the solvent. Water (50 ml.) is added, then glacial acetic acid is added, until the foaming caused by the acid ceases. The solution is evaporated to dryness in vacuo, alcohol is added and the whole evaporated to dryness in vacuo. Then 30 ml. of ethanol is added to the residue and the mixture stirred and filtered. The collected insoluble solid is air dried. This solid is heated with 300 ml. of acetone and filtered. The filtrate is concentrated in vacuo to afford 0.55 g. of the title compound, melting point 170°-176° C. On further work-up of the acetone mother liquor, 0.2 g. of the title compound, melting point 169°-174° C., is recovered.

Workup

  1. waitafter standing overnight
  2. stirringwhile stirring
  3. customThe mixture is then evaporated in vacuo
  4. customto remove the solvent
  5. additionWater (50 ml.) is added
  6. additionglacial acetic acid is added, until the foaming
  7. customThe solution is evaporated to dryness in vacuo, alcohol
  8. additionis added
  9. customthe whole evaporated to dryness in vacuo
  10. additionof ethanol is added to the residue
  11. stirringthe mixture stirred
  12. filtrationfiltered
  13. customdried
  14. temperatureThis solid is heated with 300 ml
  15. filtrationof acetone and filtered
  16. concentrationThe filtrate is concentrated in vacuo
  17. customto afford 0.55 g

Sources & evidence

ORD record
ord-d1ec4bb41e6c433fb817bedd475df3ec
Source dataset
uspto-grants-1978_05
Patent number
US04091018

Reaction notes

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