Hydrochloric Acid → HCID 19834637, compound

HRID 1087686Notes

Reaction equation

HRID 1087686 reaction equation
C([O-])(=O)C.[NH4+].Cl.[CH3:7][NH:8][C:9]1[C:10]([O:19][CH3:20])=[C:11]([NH2:18])[C:12]([O:16][CH3:17])=[C:13]([Cl:15])[CH:14]=1.C1N2CCN(CC2)C1.Cl>[Pd].O.C(OCC)(=O)C.C(O)C.C(O)=O>[ClH:15].[CH3:7][NH:8][C:9]1[CH:14]=[CH:13][C:12]([O:16][CH3:17])=[C:11]([NH2:18])[C:10]=1[O:19][CH3:20]

Participants

10

Reactant 4

HCID 313Hydrochloric AcidHCID 9237DabcoHCID 517165Ammonium AcetateHCID 19834641HCID 19834641, compound

Product 1

HCID 19834637HCID 19834637, compound

Reagents, catalysts & solvents 5

HCID 23938PalladiumCatalystHCID 284Formic AcidSolventHCID 702EthanolSolvent2×HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
70 °C

Procedure

The mixture consisting of 8.5 g of ammonium acetate, 7.5 g of 10% palladium on charcoal, 0.05 mole (15 g) of 5-methylamino-3-amino-2,4-dimethoxychlorobenzene hydrochloride in 14 ml of water containing 90 ml of ethanol and 15.2 g of triethylenediamine, was heated to 70° C. with stirring, and then 6.44 g of formic acid were added dropwise. Heating was maintained for 1 hour after completion of the addition. The catalyst was removed by filtration. The solids content obtained by evaporation of the filtrate under vacuum was dissolved in ethyl acetate. A 7N hydrochloric acid solution in absolute ethanol was added to the ethyl acetate which had been dried over sodium sulphate, in order to precipitate the expected product. The latter was recrystallized while hot from an aqueous-alcoholic solution of hydrochloric acid.

Workup

  1. temperatureHeating
  2. temperaturewas maintained for 1 hour
  3. additionafter completion of the addition
  4. customThe catalyst was removed by filtration
  5. customThe solids content obtained by evaporation of the filtrate under vacuum
  6. dry with materialhad been dried over sodium sulphate, in order
  7. customto precipitate the expected product
  8. customThe latter was recrystallized while hot from an aqueous-alcoholic solution of hydrochloric acid

Sources & evidence

ORD record
ord-4ff9e42a662843a8885220fd0e3c4ccf
Source dataset
uspto-grants-1990_10
Patent number
US04960432

Reaction notes

Loading…