Ethanol → HCID 10150564, compound

HRID 2105576Notes

Reaction equation

HRID 2105576 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:23])/[CH:11]=[CH:12]/[C:13]2[CH:18]=[CH:17][C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:15][CH:14]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].C(C1C=CC(/C=C/[C:36]([NH:38][C:39]2C=CC(Cl)=C([N+]([O-])=O)C=2)=[O:37])=CC=1)(C)(C)C.CCO.[In]>[NH4+].[Cl-]>[C:19]([C:16]1[CH:15]=[CH:14][C:13](/[CH:12]=[CH:11]/[C:10]([NH:9][C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([NH:1][C:36]([NH:38][CH3:39])=[O:37])[CH:3]=2)=[O:23])=[CH:18][CH:17]=1)([CH3:20])([CH3:22])[CH3:21]

Participants

6

Reactant 4

HCID 702EthanolHCID 1221358HCID 1221358, compoundHCID 5359967IndiumHCID 57807991HCID 57807991, compound

Product 1

HCID 10150564HCID 10150564, compound

Reagents, catalysts & solvents 1

HCID 25517Ammonium ChlorideSolvent

Procedure

(2E)-N-(3-Amino-4-chlorophenyl)-3-[4-(tert-butyl)phenyl]prop-2-enamide. To a round-bottomed flask equipped with a magnetic stir bar, was added (2E)-3-[4-(tert-butyl)phenyl]-N-(4-chloro-3-nitrophenyl)prop-2-enamide, Example 156, (250 mg, 0.69 mmol), EtOH (8 mL), indium (800 mg, 6.9 mmol, Aldrich) and satd NH4Cl (10 mL). The reaction mixture was stirred at reflux for 5 h. The solvents were removed in vacuo, the residue was dissolved in EtOAc (20 mL), washed with water (20 mL), dried over Na2SO4, filtered and concentrated in vacuo to yield the title product. MS (ESI, pos. ion) m/z: 329 (M+1).

Workup

  1. customTo a round-bottomed flask equipped with a magnetic stir bar
  2. temperatureat reflux for 5 h
  3. customThe solvents were removed in vacuo
  4. dissolutionthe residue was dissolved in EtOAc (20 mL)
  5. washwashed with water (20 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-986581e4dacd464b958dbeea6a4add7e
Source dataset
uspto-grants-2009_08
Patent number
US07579347B2

Reaction notes

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