Hydrochloric Acid → HCID 19827560, compound

HRID 1974003Notes

Reaction equation

HRID 1974003 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:4]=1[CH:5](O)[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH2:12])[CH:7]=1.Cl>[Zn].C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:4]=1[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH2:12])[CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric Acid2×HCID 23009098HCID 23009098, compound

Product 1

HCID 19827560HCID 19827560, compoundYield 76.7%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To 300 ml of acetic acid were added 96 g of zinc powder and 50 g of the 2,5-dimethoxy-3'-aminobenzhydrol prepared in (b) then 240 ml of a 35% hydrochloric acid aqueous solution was added dropwise at 80° C. After 30 minutes the same amount of the 35% hydrochloric acid solution was further added. After 2 hours of stirring, the mixture was cooled and the supernatant liquid was separated, to which an aqueous solution of sodium hydroxide was added until the pH became 5. An oily product deposited which was extracted with ethyl acetate and washed with an aqueous solution of sodium bicarbonate. Drying with sodium sulfate followed by distillation under a reduced pressure on an oil bath whereby a distillation fraction boiling in the range 170° to 175° C was collected provided 36 g of crystals with a melting point of 81° to 84° C.

Workup

  1. temperaturethe mixture was cooled
  2. customthe supernatant liquid was separated, to which an aqueous solution of sodium hydroxide
  3. additionwas added until the pH
  4. extractionwas extracted with ethyl acetate
  5. washwashed with an aqueous solution of sodium bicarbonate
  6. dry with materialDrying with sodium sulfate
  7. distillationfollowed by distillation under a reduced pressure on an oil bath whereby a distillation fraction
  8. customboiling in the range 170° to 175° C
  9. customwas collected

Sources & evidence

ORD record
ord-0c36d1b4c56949779c2261b5dce9fabb
Source dataset
uspto-grants-1976_12
Patent number
US03999991

Reaction notes

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