Water → HCID 18354826, compound

HRID 1533784Notes

Reaction equation

HRID 1533784 reaction equation
[CH2:1]([O:8][CH2:9][C:10]1[O:11][C:12]([C:14]2[C:19]([CH:20]=1)=[C:18]([N+:21]([O-])=O)[CH:17]=[CH:16][CH:15]=2)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.C(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>CO.[Cl-].[Cl-].[Cl-].[Ti+3]>[CH2:1]([O:8][CH2:9][C:10]1[O:11][C:12]([C:14]2[C:19]([CH:20]=1)=[C:18]([NH2:21])[CH:17]=[CH:16][CH:15]=2)=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6212ChloroformHCID 516892Sodium BicarbonateHCID 18355212HCID 18355212, compound

Product 1

HCID 18354826HCID 18354826, compoundYield 104.9%

Reagents, catalysts & solvents 2

HCID 10313229titanium(III) trichlorideCatalystHCID 887MethanolSolvent

Procedure

A solution of 3-benzyloxymethyl-5-nitroisocoumarin (850 mg) in methanol (40.0 ml) was treated with aqueous titanium trichloride (11.2 ml), added as a single portion. After stirring 2 hours at ambient temperature, water (100 ml) and chloroform (120 ml) were added. The whole was carefully basified with saturated sodium bicarbonate aqueous solution and the organic layer was separated. The aqueous layer was further extracted with chloroform (120 ml) and the combined extract was washed with water, dried over magnesium sulfate, and concentrated to afford 3-benzyloxymethyl-5-aminoisocoumarin (806 mg).

Workup

  1. additionadded as a single portion
  2. customthe organic layer was separated
  3. extractionThe aqueous layer was further extracted with chloroform (120 ml)
  4. extractionthe combined extract
  5. washwas washed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a7a4032dd7e34b60a6796982bc973f66
Source dataset
uspto-grants-2001_03
Patent number
US06207693B1

Reaction notes

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