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 372391Notes

Reaction equation

HRID 372391 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 /0.05 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-579d3abe9fc14060aff2e17fd605902b
Source dataset
uspto-grants-1978_05
Patent number
US04091018

Reaction notes

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