4-Nitrobenzaldehyde → 6-Acetylamino-3-methyl-1-(4-nitrophenyl)-7-methoxyisochroman

HRID 2179893Notes

Reaction equation

HRID 2179893 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH2:13][CH:14]([OH:16])[CH3:15])[CH:8]=[CH:9][C:10]=1[O:11][CH3:12])(=[O:3])[CH3:2].[N+:17]([C:20]1[CH:27]=[CH:26][C:23]([CH:24]=O)=[CH:22][CH:21]=1)([O-:19])=[O:18]>Cl.O1CCOCC1>[C:1]([NH:4][C:5]1[CH:6]=[C:7]2[C:8](=[CH:9][C:10]=1[O:11][CH3:12])[CH:24]([C:23]1[CH:26]=[CH:27][C:20]([N+:17]([O-:19])=[O:18])=[CH:21][CH:22]=1)[O:16][CH:14]([CH3:15])[CH2:13]2)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 5414-NitrobenzaldehydeHCID 697337221-(3-Acetylamino-4-methoxyphenyl)-2-propyl Alcohol

Product 1

HCID 224889656-Acetylamino-3-methyl-1-(4-nitrophenyl)-7-methoxyisochromanYield 66%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of compound 13 (0.23 g, 1.03 mmol) in 15 ml of HCl solution in 1,4-dioxane was added 4-nitrobenzaldehyde (0.16 g, 1.06 mmol) in one portion. After refluxing for 5 hours, the solvent was removed under reduced pressure. The residue was washed with cold ethanol three times, and dried to give the product 14 (0.21 g, 66%).

Workup

  1. temperatureAfter refluxing for 5 hours
  2. customthe solvent was removed under reduced pressure
  3. washThe residue was washed with cold ethanol three times
  4. customdried

Sources & evidence

ORD record
ord-d67cf6e48b9e43c7bd676093637a3d43
Source dataset
uspto-grants-2005_05
Patent number
US06887867B2

Reaction notes

Loading…