Water → HCID 19834634, compound

HRID 1087688Notes

Reaction equation

HRID 1087688 reaction equation
C([O-])(=O)C.[NH4+].Cl.[CH3:7][O:8][C:9]1[C:14]([NH2:15])=[C:13]([O:16][CH3:17])[C:12]([NH2:18])=[CH:11][C:10]=1[Cl:19].O.C(N(CC)CC)C>[Pd].C(O)C.C(O)=O>[ClH:19].[NH2:15][C:14]1[C:13]([O:16][CH3:17])=[C:12]([NH2:18])[CH:11]=[CH:10][C:9]=1[O:8][CH3:7]

Participants

8

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 517165Ammonium AcetateHCID 19834645HCID 19834645, compound

Product 1

HCID 19834634HCID 19834634, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 284Formic AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

The mixture consisting of 77 g of ammonium acetate, 42 g of 10% palladium on charcoal, 0.25 mole (69 g) of 2,4-dimethoxy-3,5-diaminochlorobenzene hydrochloride in 420 ml of ethanol containing 50 ml of water was heated to 75° C. with stirring. 75 g of triethylamine were added and then, 31 g of formic acid were added dropwise. After 30 minutes of additional heating, the reaction mixture was filtered while hot. The filtrate was evaporated to dryness. Upon addition of ethyl acetate, the inorganic salts were precipitated and removed by thorough draining. 10 ml of an alcoholic solution of 7N hydrochloric acid were added to the filtrate which had been dried over sodium sulphate. The expected product precipitated, it was recrystallized from a mixture of water and a solution of hydrochloric acid in ethanol.

Workup

  1. filtrationthe reaction mixture was filtered while hot
  2. customThe filtrate was evaporated to dryness
  3. additionUpon addition of ethyl acetate
  4. customthe inorganic salts were precipitated
  5. customremoved by thorough draining
  6. addition10 ml of an alcoholic solution of 7N hydrochloric acid were added to the filtrate which
  7. dry with materialhad been dried over sodium sulphate
  8. customThe expected product precipitated
  9. customit was recrystallized from a mixture of water

Sources & evidence

ORD record
ord-5f8716179c994e869ae395c034229a4d
Source dataset
uspto-grants-1990_10
Patent number
US04960432

Reaction notes

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