Hydrochloric Acid → 6-Acetylamino-1-hydroxy-3-methyl-1-(4-nitrophenyl)-7-methoxyisochroman

HRID 2179897Notes

Reaction equation

HRID 2179897 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[CH:11]([C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=1)[O:10][CH:9]([CH3:26])[CH2:8]2)(=[O:3])[CH3:2].[OH-:27].[Na+].Cl>CS(C)=O.CN(C=O)C>[C:1]([NH:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[C:11]([OH:27])([C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=1)[O:10][CH:9]([CH3:26])[CH2:8]2)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 224889656-Acetylamino-3-methyl-1-(4-nitrophenyl)-7-methoxyisochroman

Product 1

HCID 224889686-Acetylamino-1-hydroxy-3-methyl-1-(4-nitrophenyl)-7-methoxyisochroman

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 14 (1.8 g) in 5 ml of DMSO and 30 ml of DMF was cooled to 8-12° C. and air was passed through the mixture. To the solution was added 1.2 ml of 50% aqueous sodium hydroxide in one portion and the resulting mixture was stirred for 5 hours. HCl (1 N) was added, and extracted with ethyl acetate three times. The combined organic phase was washed with water, dried over Na2SO4. Removal of the solvent afforded 22 (1.9 g) as a syrup, which was used directly for the next step.

Workup

  1. extractionextracted with ethyl acetate three times
  2. washThe combined organic phase was washed with water
  3. dry with materialdried over Na2SO4
  4. customRemoval of the solvent

Sources & evidence

ORD record
ord-ea9305c7537b42d1856ce2e786c2112e
Source dataset
uspto-grants-2005_05
Patent number
US06887867B2

Reaction notes

Loading…