Hydrochloric Acid → HCID 59597225, compound

HRID 218638Notes

Reaction equation

HRID 218638 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH2:9][CH:10]2[C:13]([OH:15])=O)=[CH:5][CH:4]=1.C([O:18][CH:19](OCC)[C:20]1[CH:25]=[CH:24][C:23]([CH2:26][NH:27][C:28]2[CH:33]=[CH:32][C:31]([CH:34]([CH3:36])[CH3:35])=[CH:30][CH:29]=2)=[CH:22][CH:21]=1)C.Cl>CO>[CH:19]([C:20]1[CH:21]=[CH:22][C:23]([CH2:26][N:27]([C:28]2[CH:33]=[CH:32][C:31]([CH:34]([CH3:36])[CH3:35])=[CH:30][CH:29]=2)[C:13]([CH:10]2[C:11]3[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=3)[CH2:7][CH2:8][CH2:9]2)=[O:15])=[CH:24][CH:25]=1)=[O:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 132774847-Methoxy-1,2,3,4-tetrahydronaphthalene-1-carboxylic acidHCID 67183344HCID 67183344, compound

Product 1

HCID 59597225HCID 59597225, compoundYield 47.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

By the reaction and treatment in the same manner as in Example 12 using 7-methoxy-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid (0.41 g) and {[4-(diethoxymethyl)phenyl]-methyl}(4-isopropylphenyl)amine (0.65 g) as starting materials. The obtained residue was dissolved in a mixed solvent (15 mL) of methanol:1 mol/L-hydrochloric acid (1:2) and heated under reflux for 3 hr. The reaction mixture was concentrated under reduced pressure and partitioned between water and ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was purified by silica gel column chromatography to give N-[(4-formylphenyl)methyl]-N-(4-isopropylphenyl)-7-methoxy-1,2,3,4-tetrahydronaphthalene-1-carboxamide (0.42 g).

Workup

  1. temperatureunder reflux for 3 hr
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. custompartitioned between water and ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-89bcfe07d22148c184aaf2d7d879a1df
Source dataset
uspto-grants-2012_06
Patent number
US08198454B2

Reaction notes

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