(E)-N-(3,3-Dimethyl-6-nitro-2-oxo-1-pentyl-2,3-dihydro-1H-indol-5-yl)-3-(2-nitro-phenyl)-acrylamide → (E)-N-(6-Amino-3,3-dimethyl-2-oxo-1-pentyl-2,3-dihydro-1H-indol-5-yl)-3-(2-amino-phenyl)-acrylamide

HRID 2235405Notes

Reaction equation

HRID 2235405 reaction equation
[CH3:1][C:2]1([CH3:34])[C:10]2[C:5](=[CH:6][C:7]([N+:25]([O-])=O)=[C:8]([NH:11][C:12](=[O:24])/[CH:13]=[CH:14]/[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N+:21]([O-])=O)[CH:9]=2)[N:4]([CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[C:3]1=[O:33].Cl[Sn]Cl.O>CCOC(C)=O>[NH2:25][C:7]1[CH:6]=[C:5]2[C:10]([C:2]([CH3:1])([CH3:34])[C:3](=[O:33])[N:4]2[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[CH:9][C:8]=1[NH:11][C:12](=[O:24])/[CH:13]=[CH:14]/[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[NH2:21]

Participants

4

Reactant 2

HCID 23092686(E)-N-(3,3-Dimethyl-6-nitro-2-oxo-1-pentyl-2,3-dihydro-1H-indol-5-yl)-3-(2-nitro-phenyl)-acrylamideHCID 43835034Tin dichloride dihydrate

Product 1

HCID 23092671(E)-N-(6-Amino-3,3-dimethyl-2-oxo-1-pentyl-2,3-dihydro-1H-indol-5-yl)-3-(2-amino-phenyl)-acrylamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(E)-N-(3,3-Dimethyl-6-nitro-2-oxo-1-pentyl-2,3-dihydro-1H-indol-5-yl)-3-(2-nitrophenyl)-acrylamide is dissolved in EtOAc (70 ml). SnCl2.H2O (5.44 g; 24.1 mmol) is added and the resulting mixture is heated under reflux for 20 h. After re-cooling the mixture is filtered over basic Al2O3 (120 g) and concentrated in vacuo. The residue is taken-up in EtOAc and saturated K2CO3 solution. After an aqueous work-up the compound (0.82 g) is obtained as a yellow solid.

Workup

  1. temperaturethe resulting mixture is heated
  2. temperatureunder reflux for 20 h
  3. temperatureAfter re-cooling the mixture
  4. filtrationis filtered over basic Al2O3 (120 g)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bf420c25da0d4165b8088eb3f9aa2f08
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

Loading…