N-Methyl-N'-(4-oxo-1,2,3,4-tetrahydronaphthalen-1-yl)urea → 1-Methyl-3-(1,2,3,4-tetrahydro-4-hydroxy-1-naphthyl)urea

HRID 2072146Notes

Reaction equation

HRID 2072146 reaction equation
[CH3:1][NH:2][C:3]([NH:5][CH:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:16])[CH2:8][CH2:7]1)=[O:4]>O=[Pt]=O.C(O)C>[CH3:1][NH:2][C:3]([NH:5][CH:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]([OH:16])[CH2:8][CH2:7]1)=[O:4]

Participants

4

Reactant 1

HCID 20327317N-Methyl-N'-(4-oxo-1,2,3,4-tetrahydronaphthalen-1-yl)urea

Product 1

HCID 203273191-Methyl-3-(1,2,3,4-tetrahydro-4-hydroxy-1-naphthyl)urea

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

1-Methyl-3-(1,2,3,4-tetrahydro-4-oxo-1-naphthyl)-urea (3.3 g.) is hydrogenated in the presence of 0.3 g. of PtO2 10.05 mmole FeCl3 solution in 300 ml. of 95% ethanol using a low-pressure all-glass hydrogenator. After 615 ml. of hydrogen is absorbed, the excess hydrogen is removed by purging the system with nitrogen. The solution is filtered and evaporated to dryness in vacuo to afford 3.4 g. of an oil. The oil is stirred with about 20 ml. of acetone and the formed white solid is collected to afford 1.6 g. of the title compound as a cis/trans mixture, melting point 172°-180° C.

Workup

  1. customof hydrogen is absorbed
  2. customthe excess hydrogen is removed
  3. customby purging the system with nitrogen
  4. filtrationThe solution is filtered
  5. customevaporated to dryness in vacuo
  6. customto afford 3.4 g
  7. customof acetone and the formed white solid is collected
  8. customto afford 1.6 g

Sources & evidence

ORD record
ord-f6e83af30b2d4942bea2bdca8d1f6789
Source dataset
uspto-grants-1977_09
Patent number
US04049717

Reaction notes

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