Sulfuric Acid → HCID 54703873, compound

HRID 372017Notes

Reaction equation

HRID 372017 reaction equation
S(=O)(=O)(O)O.O[CH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:16])[N:8]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[OH:23][C:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[O:27][C:26](=[O:34])[CH:25]=1>C(O)(=O)C.CN(C)C=O>[OH:23][C:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[O:27][C:26](=[O:34])[C:25]=1[CH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:16])[N:8]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 866702,3-Dihydro-3-hydroxy-2-phenyl-1H-isoindol-1-oneHCID 546829304-Hydroxycoumarin

Product 1

HCID 54703873HCID 54703873, compoundYield 85.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

Sulphuric acid (210 cc) is added dropwise to a suspension of 3-hydroxy-2-phenylisoindolin-1-one (67.5 g) and 4-hydroxycoumarin (97.3 g) in acetic acid (675 cc) whilst maintaining the temperature between 15° and 18° C, and the mixture is stirred for 15 hours at a temperature of about 20° C. The reaction mixture is then run into icewater (3000 cc) and the precipitate is filtered off and washed with water (2500 cc). The filter cake is dried in a stream of air at a temperature of about 20° C. The product obtained is dissolved in dimethylformamide (800 cc) at 90° C. The solution is filtered and acetonitrile (900 cc) is then added. After cooling in an ice-bath for 2 hours, the solid is filtered off and washed with acetonitrile (1000 cc). It is dried under reduced pressure (0.1 mm Hg) for 15 hours at 20° C and then for 4 hours at 55° C and 2 hours at 80° C. 3-(4-Hydroxycoumarin-3-yl)-2-phenylisoindolin-1-one (95 g), melting at 335°-337° C, is thus obtained.

Workup

  1. temperaturewhilst maintaining the temperature between 15° and 18° C
  2. filtrationthe precipitate is filtered off
  3. washwashed with water (2500 cc)
  4. customThe filter cake is dried in a stream of air at a temperature of about 20° C
  5. customThe product obtained
  6. filtrationThe solution is filtered
  7. additionacetonitrile (900 cc) is then added
  8. temperatureAfter cooling in an ice-bath for 2 hours
  9. filtrationthe solid is filtered off
  10. washwashed with acetonitrile (1000 cc)
  11. customIt is dried under reduced pressure (0.1 mm Hg) for 15 hours at 20° C
  12. waitfor 4 hours at 55° C
  13. custom2 hours
  14. customat 80° C

Sources & evidence

ORD record
ord-01bef9ffe14f4fa9adfd404c3f8c80d4
Source dataset
uspto-grants-1978_05
Patent number
US04088774

Reaction notes

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