Isatin → HCID 15085959, compound

HRID 1073259Notes

Reaction equation

HRID 1073259 reaction equation
[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=O)[C:2]1=[O:3].[OH-:12].[Na+].[NH2:14][CH2:15][C:16]([C:18]1[CH:23]=[CH:22][C:21](C2C=CC=CC=2)=[CH:20][CH:19]=1)=O.[O:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1.[CH2:35](O)[CH3:36].O>O>[NH2:14][C:15]1[C:16]([C:18]2[CH:19]=[CH:20][C:21]([O:30][C:34]3[CH:33]=[CH:32][CH:31]=[CH:36][CH:35]=3)=[CH:22][CH:23]=2)=[N:1][C:11]2[C:6]([C:4]=1[C:2]([OH:12])=[O:3])=[CH:7][CH:8]=[CH:9][CH:10]=2

Participants

7

Reactant 5

HCID 7054Isatin2×HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 422187HCID 422187, compoundHCID 19096565Water ethanol

Product 1

HCID 15085959HCID 15085959, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
90 °C

Procedure

A 3.68 g portion of isatin was suspended in 36 ml of water. A solution of 5.62 g of sodium hydroxide in 20 ml of water was added and the mixture was heated to 90° C. A solution of 9.24 g of 2-amino-4'-phenylacetophenone in 122 ml of ethanol:water (1:1), containing sufficient tetrahydrofuran to effect solution was added dropwise to the isatin solution over 2 hours. This mixture was stirred at reflux for 2 hours, then the solvent was distilled off. The remaining solution was cooled in an ice bath, then filtered and the filtrate acidified to pH 5. The resulting solid was collected, washed with water and air dried, then recrystallized from acetonitrile. This solid was suspended in 200 ml of water, basified with sodium hydroxide and extracted with dichloromethane. The aqueous remainder was filtered and the filtrate acidified to pH 3 with glacial acetic acid. The solid was collected and dried in vacuo, giving 3.80 g of the desired product, mp 218°-220° C.

Workup

  1. temperatureat reflux for 2 hours
  2. distillationthe solvent was distilled off
  3. temperatureThe remaining solution was cooled in an ice bath
  4. filtrationfiltered
  5. customThe resulting solid was collected
  6. washwashed with water and air
  7. customdried
  8. customrecrystallized from acetonitrile
  9. extractionextracted with dichloromethane
  10. filtrationThe aqueous remainder was filtered
  11. customThe solid was collected
  12. customdried in vacuo

Sources & evidence

ORD record
ord-c91e4614ffcb4b8db8d6933b21117420
Source dataset
uspto-grants-1990_11
Patent number
US04968702

Reaction notes

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