Methane → HCID 14209232, compound

HRID 1252395Notes

Reaction equation

HRID 1252395 reaction equation
Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][CH2:13][CH:14]([OH:21])[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.C.C([O-])(=O)C.[Na+].[H][H]>[Pd].CO.C(O)(=O)C>[OH:21][CH:14]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:13][NH:12][C:6]1[C:5]2[C:10](=[CH:11][CH:2]=[CH:3][CH:4]=2)[N:9]=[CH:8][CH:7]=1

Participants

8

Reactant 4

HCID 297MethaneHCID 517045Sodium AcetateHCID 14209230HCID 14209230, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14209232HCID 14209232, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A mixture of 7-chloro-N-(2-hydroxy-2-phenylethyl)-4-quinolinamine (10 g), 0.8 g of palladium on powdered charcoal (10%), 5 ml of acetic acid, 7 g of sodium acetate.3H2O and 200 ml of methanol was hydrogenated at room temperature with shaking at 30-50 psi until completion of hydrogen uptake. The catalyst was filtered and the solvent evaporated. The oil residue was dissolved in 20 ml of water and the solution made alkaline (pH=10) with and NaOH solution. The crystalline compound was filtered and recrystallized from isopropanol. The yield was 7.5 g, mp 289°-290° C.

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationThe catalyst was filtered
  3. customthe solvent evaporated
  4. dissolutionThe oil residue was dissolved in 20 ml of water
  5. filtrationThe crystalline compound was filtered
  6. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-f1dffe9e2fce483d8fa718e4fd480f78
Source dataset
uspto-grants-1988_05
Patent number
US04743601

Reaction notes

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