Reaction HRID 1578467

HRID 1578467Notes

Reaction equation

HRID 1578467 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10](=[O:13])(=[O:12])=[O:11])[CH:5]=1)([O-])=O>C(O)C.Cl>[ClH:10].[Cl:10]([C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[NH2:1])(=[O:13])(=[O:12])=[O:11]

Participants

2

Reactant 0

No Reactant data yet.

Product 0

No Product data yet.

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

To a stirred solution of 268 grams (1.3 moles) of II in 1.5 liters of ethanol and 1.5 liters of concentrated hydrochloric acid, 850 grams (4.5 moles) of stannous chloride was added in portions, the mixture being maintained at 50°-60° by heating. The mixture was held at 60° for 2 hours after the last of the stannous chloride had been added. The resulting mixture was concentrated under reduced pressure (25 torr., 75°-85°), then poured over ice and water and neutralized to a pH of 5-6 with sodium hydroxide solution. The resulting suspension was extracted repeatedly with ether. The combined ether extracts were dried, filtered and then treated with dry hydrogen chloride to give 95 grams (34% yield) of III, as a light-tan crystalline solid, melting with decomposition at 177°-178°.

Workup

  1. temperaturethe mixture being maintained at 50°-60°
  2. temperatureby heating
  3. concentrationThe resulting mixture was concentrated under reduced pressure (25 torr., 75°-85°)
  4. additionpoured over ice and water and neutralized to a pH of 5-6 with sodium hydroxide solution
  5. extractionThe resulting suspension was extracted repeatedly with ether
  6. dry with materialThe combined ether extracts were dried
  7. filtrationfiltered
  8. additiontreated with dry hydrogen chloride

Sources & evidence

ORD record
ord-b55f1067098144aba144a7378272c1e3
Source dataset
uspto-grants-1976_02
Patent number
US03937627

Reaction notes

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