Ethanol → HCID 10150564, compound

HRID 730271Notes

Reaction equation

HRID 730271 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-267069a98edd4c74a3f9823510aa6499
Source dataset
uspto-grants-2009_09
Patent number
US07582657B2

Reaction notes

Loading…