Water → HCID 18354826, compound

HRID 429657Notes

Reaction equation

HRID 429657 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) was 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-7fe3a92749f2496998137f2ba483aa90
Source dataset
uspto-grants-2001_11
Patent number
US06316482B1

Reaction notes

Loading…