Sodium Hydroxide → HCID 15085975, compound

HRID 1073278Notes

Reaction equation

HRID 1073278 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=O.[OH-:13].[Na+].Cl.[NH2:16][CH2:17][C:18]([C:20]1[CH:25]=[CH:24][C:23]([I:26])=[CH:22][CH:21]=1)=O>O.C(O)C.O1CCCC1>[NH2:16][C:17]1[C:18]([C:20]2[CH:25]=[CH:24][C:23]([I:26])=[CH:22][CH:21]=2)=[N:7][C:8]2[C:4]([C:5]=1[C:6]([OH:11])=[O:13])=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=2

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 872035-chloro-1H-indole-2,3-dioneHCID 221583482-Amino-1-(4-iodophenyl)ethan-1-one--hydrogen chloride (1/1)

Product 1

HCID 15085975HCID 15085975, compoundYield 66.7%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent3×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
85 °C

Procedure

To a stirred suspension of 4.17 g of 5-chloroisatin in 40 ml of water was added a solution of 5.15 g of sodium hydroxide in 18 ml of water. The solution was heated to 85° C. and a solution of 9.8 g of 2-amino-1-(4-iodophenyl)ethanone hydrochloride in a mixture of 70 ml of ethanol and 30 ml of tetrahydrofuran and 130 ml of water was added dropwise over 2 hours. After the addition was complete, the solution was refluxed for an additional 30 minutes and then the ethanol and tetrahydrofuran were removed by distillation. The mixture was cooled to 20° C. and filtered through celite. The filtrate was acidified to pH 4 with acetic acid. The solid was filtered off, washed with water and dried, giving 6.5 g of the desired compound as a yellow solid, mp 243°-245° C.

Workup

  1. additionwas added dropwise over 2 hours
  2. additionAfter the addition
  3. temperaturethe solution was refluxed for an additional 30 minutes
  4. customthe ethanol and tetrahydrofuran were removed by distillation
  5. temperatureThe mixture was cooled to 20° C.
  6. filtrationfiltered through celite
  7. filtrationThe solid was filtered off
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-7bdf3dcbea50403bb8a0ad40565cabca
Source dataset
uspto-grants-1990_11
Patent number
US04968702

Reaction notes

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