Sulfuric Acid → HCID 13105508, compound

HRID 370728Notes

Reaction equation

HRID 370728 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11](N)=[CH:10][C:9]=2[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:16])[CH2:4][CH2:3]1.S(=O)(=O)(O)O.N([O-])=O.[Na+]>C(O)C.[Cu]>[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:16])[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 13105516HCID 13105516, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 13105508HCID 13105508, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

0.01 mole (3 g) of [2-(4-methyl-1-piperidinyl)-5-aminophenyl]-phenyl-methanone (product of example 27; Code No. 592) is dissolved in ethanol. The mixture is cooled to 0° C. then 10 ml of sulphuric acid and 0.02 mole (1.4 g) of sodium nitrite are successively added. The mixture is stirred for 1 hour at 0° C. then allowed to return to room temperature (15°-20° C.). 0.65 g of activated copper is then added and the reaction medium is heated to 50° C. for 1 hour. After hydrolysis and neutralization, it is extracted with methylene chloride then washed with water. It is dried then the solvent is evaporated. By recrystallization from ethanol, 1 g (yield=37%) of the expected product is obtained. M.p.=82° C.

Workup

  1. customto return to room temperature
  2. custom(15°-20° C.)
  3. temperaturethe reaction medium is heated to 50° C. for 1 hour
  4. customAfter hydrolysis and neutralization, it
  5. extractionis extracted with methylene chloride
  6. washthen washed with water
  7. customIt is dried
  8. customthe solvent is evaporated
  9. customBy recrystallization from ethanol

Sources & evidence

ORD record
ord-66d998192f6746e9b89e158935ea1153
Source dataset
uspto-grants-1985_07
Patent number
US04528294

Reaction notes

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