Hydrochloric Acid → 2-Aminobenzophenone

HRID 1061861Notes

Reaction equation

HRID 1061861 reaction equation
C1(C)C(S([C:10]2[CH:11]=[C:12]([NH2:19])[C:13](=[CH:17][CH:18]=2)[C:14]([OH:16])=O)(=O)=O)=CC=CC=1.P(Cl)(Cl)(Cl)(Cl)Cl.[Cl-].[Al+3].[Cl-].[Cl-].Cl>C1C=CC=CC=1>[NH2:19][C:12]1[CH:11]=[CH:10][CH:18]=[CH:17][C:13]=1[C:14]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:17][CH:18]=1)=[O:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24819Phosphorus pentachlorideHCID 6451240Aluminum(III) ChlorideHCID 69747102HCID 69747102, compound

Product 1

HCID 760802-AminobenzophenoneYield 134.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
50 °C

Procedure

The mixture of 14.6 g (0.050 mol) of p-toluenesulfonylanthranilic acid prepared in Example 8 and 11.9 g (0.057 mol) of phosphorus pentachloride in 150 ml of dry benzene were heated at about 50° C. for 0.5 h. Cooled to 20-25° C. and 29.0 g (0.218 mol) of anhydrous aluminum chloride was added in portions. When addition was complete, the mixture was heated at 80-90° C. for 4 h and then cooled, poured onto a mixture of ice and 60 ml of 1N hydrochloride acid. The benzene was removed by vacuo distillation, the crude product was separated by filtration and washed with sodium carbonate and water. The filter cake is sucked reasonably dry, dissolved in 160 ml of conc. sulfuric acid and heated to 120° C. for 15 minutes. The reaction mixture was cooled and poured onto the mixture of ice and 1 g of norit, and the solution is filtered. The filtrate was neutralized with 12N ammonium hydroxide. The solid filtered off, washed with water and dried, recrystallized from 95% ethanol to give the title compound (6.63 g) as yellow crystal, yield 65.0%, m.p. 105-106° C.

Workup

  1. temperatureCooled to 20-25° C.
  2. additionWhen addition
  3. temperaturethe mixture was heated at 80-90° C. for 4 h
  4. temperaturecooled
  5. customThe benzene was removed by vacuo distillation
  6. customthe crude product was separated by filtration
  7. washwashed with sodium carbonate and water
  8. customThe filter cake is sucked reasonably dry
  9. dissolutiondissolved in 160 ml of conc. sulfuric acid
  10. temperatureheated to 120° C. for 15 minutes
  11. temperatureThe reaction mixture was cooled
  12. additionpoured onto the mixture of ice and 1 g of norit
  13. filtrationthe solution is filtered
  14. filtrationThe solid filtered off
  15. washwashed with water
  16. customdried
  17. customrecrystallized from 95% ethanol

Sources & evidence

ORD record
ord-7ce5089bb88e46bbb11accd7debb16be
Source dataset
uspto-grants-2005_11
Patent number
US06960611B2

Reaction notes

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