Hydrogen Peroxide → HCID 13651753, compound

HRID 569683Notes

Reaction equation

HRID 569683 reaction equation
[CH3:1][N:2]([CH3:30])[C:3]1[CH:29]=[CH:28][C:6]([CH:7]([C:16]2[CH:24]=[CH:23][C:22]([N:25]([CH3:27])[CH3:26])=[CH:21][C:17]=2[C:18]([OH:20])=[O:19])[C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.O.[OH-].[Na+].OO>C(O)(C)C>[CH3:30][N:2]([CH3:1])[C:3]1[CH:4]=[CH:5][C:6]([C:7]2([C:8]3[CH:9]=[CH:10][C:11]([O:14][CH3:15])=[CH:12][CH:13]=3)[C:16]3[C:17](=[CH:21][C:22]([N:25]([CH3:27])[CH3:26])=[CH:23][CH:24]=3)[C:18](=[O:20])[O:19]2)=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 14798Sodium HydroxideHCID 13651738HCID 13651738, compound

Product 1

HCID 13651753HCID 13651753, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A stirred mixture of 8.1 g of 2-(4-dimethylamino-4'-methoxybenzhydryl)-5-dimethylaminobenzoic acid from part A above, 40.0 ml of water, 1.6 g of 50 percent aqueous sodium hydroxide and 2.7 ml of isopropyl alcohol was maintained at a temperature in the range of 85°-96° C. while 20.3 g of ten percent aqueous hydrogen peroxide was added over a period of approximately six hours. The reaction mixture was set aside at ambient temperature overnight. The solid was collected by filtration, washed free of alkali with water and dried in vacuo to obtain 5.5 g of 3-(4-dimethylaminophenyl)-3-(4-methoxyphenyl)-6-dimethylaminophthalide, a yellow-colored solid which melted at 156°-161° C.

Workup

  1. additionwas added over a period of approximately six hours
  2. filtrationThe solid was collected by filtration
  3. washwashed free of alkali with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-ed8c4e53640e4f85b451bee47ce66a52
Source dataset
uspto-grants-1988_03
Patent number
US04732991

Reaction notes

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