Hydrochloric Acid → HCID 59597303, compound

HRID 2265461Notes

Reaction equation

HRID 2265461 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([N+:32]([O-])=O)=[CH:28][CH:27]=2)[C:11]([CH:13]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([O:23][CH3:24])[CH:21]=3)[CH2:16][CH2:15][CH2:14]2)=[O:12])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].Cl>C(O)C>[NH2:32][C:29]1[CH:30]=[CH:31][C:26]([CH2:25][N:10]([C:7]2[CH:6]=[CH:5][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:9][CH:8]=2)[C:11]([CH:13]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([O:23][CH3:24])[CH:21]=3)[CH2:16][CH2:15][CH2:14]2)=[O:12])=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 16678267HCID 16678267, compound

Product 1

HCID 59597303HCID 59597303, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-(4-Isopropylphenyl)-7-methoxy-N-[(4-nitrophenyl)methyl]-1,2,3,4-tetrahydronaphthalene-1-carboxamide (1.2 g) was dissolved in ethanol (8.1 mL), and stannic chloride (1.5 g) and conc. hydrochloric acid (2.7 mL) were added. The mixture was heated under reflux for 3 hr. The reaction mixture was concentrated under reduced pressure, and the residue was partitioned between water and ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogencarbonate and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained solid was recrystallized from a mixed solvent of chloroform and diisopropyl ether to give N-[(4-aminophenyl)methyl]-N-(4-isopropylphenyl)-7-methoxy-1,2,3,4-tetrahydronaphthalene-1-carboxamide (1.0 g).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 3 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was partitioned between water and ethyl acetate
  5. washThe organic layer was washed with saturated aqueous sodium hydrogencarbonate
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe obtained solid was recrystallized from a mixed solvent of chloroform and diisopropyl ether

Sources & evidence

ORD record
ord-f147c7c15bdd4397a54a923ab8cd24ea
Source dataset
uspto-grants-2010_12
Patent number
US07855297B2

Reaction notes

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