Stannous chloride dihydrate → 1-(4,5-Diamino-2-chloro-phenyl)-pyrrolidine-3-carbonitrile

HRID 1258662Notes

Reaction equation

HRID 1258662 reaction equation
O.O.[Sn](Cl)Cl.[NH2:6][C:7]1[C:8]([N+:21]([O-])=O)=[CH:9][C:10]([Cl:20])=[C:11]([N:13]2[CH2:17][CH2:16][CH:15]([C:18]#[N:19])[CH2:14]2)[CH:12]=1>CCOC(C)=O.O.N>[NH2:21][C:8]1[C:7]([NH2:6])=[CH:12][C:11]([N:13]2[CH2:17][CH2:16][CH:15]([C:18]#[N:19])[CH2:14]2)=[C:10]([Cl:20])[CH:9]=1

Participants

6

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 679578281-(5-Amino-2-chloro-4-nitro-phenyl)-pyrrolidine-3-carbonitrile

Product 1

HCID 679576781-(4,5-Diamino-2-chloro-phenyl)-pyrrolidine-3-carbonitrile

Reagents, catalysts & solvents 3

HCID 222AmmoniaSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

Tin dichloride dihydrate (410 mg, 1.8 mmol) was added to 1-(5-amino-2-chloro-4-nitro-phenyl)-pyrrolidine-3-carbonitrile (100 mg, 0.4 mmol) in EtOAc (5 mL). The reaction mixture was stirred at reflux for 1.5 h, cooled, diluted with EtOAc and water and basified with conc. ammonia. The mixture was filtered through a pad of celite. The organic layer was dried over Na2SO4 and concentrated to give the sub-title compound.

Workup

  1. temperatureat reflux for 1.5 h
  2. temperaturecooled
  3. filtrationThe mixture was filtered through a pad of celite
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1f408d0685384336be2e90c87855920d
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

Loading…