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

HRID 372273Notes

Reaction equation

HRID 372273 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.[BH4-].[Na+].O>C(O)C>[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 962WaterHCID 3628438Urea, (1,2,3,4-tetrahydro-4-oxo-1-naphthalenyl)-HCID 4311764Sodium borohydride

Product 1

HCID 42945181,2,3,4-Tetrahydro-4-hydroxy-1-naphthylureaYield 11.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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. additionThen 30 ml of ethanol is added to the residue
  11. stirringthe mixture stirred
  12. filtrationfiltered
  13. customdried
  14. temperatureThis solid is heated with 300 ml of acetone
  15. filtrationfiltered
  16. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-3f023918618e4006ac626d1d7ebe2c94
Source dataset
uspto-grants-1978_05
Patent number
US04089976

Reaction notes

Loading…