Water → HCID 14074974, compound

HRID 1607475Notes

Reaction equation

HRID 1607475 reaction equation
C([O-])(=O)C.[NH4+].[ClH:6].Cl.[CH3:8][O:9][C:10]1[C:15]([NH2:16])=[C:14]([O:17][CH3:18])[C:13]([NH2:19])=[CH:12][C:11]=1[Cl:20].O.C(N(CC)CC)C>[Pd].C(O)C.C(O)=O>[ClH:20].[ClH:6].[NH2:16][C:15]1[C:14]([O:17][CH3:18])=[C:13]([NH2:19])[CH:12]=[CH:11][C:10]=1[O:9][CH3:8]

Participants

8

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 517165Ammonium AcetateHCID 19751963HCID 19751963, compound

Product 1

HCID 14074974HCID 14074974, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 284Formic AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

A mixture consisting of 77 g of ammonium acetate, 42 g of palladium on charcoal (10% palladium) and 0.25 mole (69 g) of 2,4-dimethoxy-3,5-diaminochlorobenzene dihydrochloride in 420 ml of ethanol to which 50 ml of water have been added is heated to 75° C. with stirring. 75 g of triethylamine are added, followed, dropwise, by 31 g of formic acid. After a further 30 minutes' heating, the reaction medium is filtered hot. The filtrate is evaporated to dryness. On addition of ethyl acetate, the inorganic salts are precipitated, and these are removed by filtration with suction. To the filtrate, dried over sodium sulphate, 100 ml of a 7N alcoholic solution of hydrochloric acid are added. The expected product precipitates, and is recrystallized from a mixture of water and a solution of hydrochloric acid in ethanol.

Workup

  1. additionhave been added
  2. temperatureAfter a further 30 minutes' heating
  3. filtrationthe reaction medium is filtered hot
  4. customThe filtrate is evaporated to dryness
  5. additionOn addition of ethyl acetate
  6. customthe inorganic salts are precipitated
  7. customthese are removed by filtration with suction
  8. dry with materialTo the filtrate, dried over sodium sulphate, 100 ml of a 7N alcoholic solution of hydrochloric acid
  9. additionare added
  10. customThe expected product precipitates
  11. customis recrystallized from a mixture of water

Sources & evidence

ORD record
ord-189054bd31574d0fac21225fea6db445
Source dataset
uspto-grants-1989_09
Patent number
US04865619

Reaction notes

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