Stannous chloride dihydrate → HCID 22382615, compound

HRID 1372437Notes

Reaction equation

HRID 1372437 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([N+:20]([O-])=O)[CH:18]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.O.[Sn](Cl)Cl>C(O)C>[NH2:20][C:17]1[CH:18]=[C:19]2[C:14]([CH2:13][CH2:12][N:11]2[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 22382567Phenylmethyl 2,3-dihydro-6-nitro-1H-indole-1-carboxylate

Product 1

HCID 22382615HCID 22382615, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1-benzyloxycarbonyl-2,3-dihydro-6-nitroindole (1.0 g, 3.36 mmol) and tin(II) chloride dihydrate (3.78 g, 16.75 mmol) in ethanol (70 mL) was heated at 70° C., under an atmosphere of nitrogen, for 3 hours. The solution was cooled and the solvent evaporated under reduced pressure to give an off-white solid. The solid was partitioned between water (50 mL) and ethyl actate (100 mL) and the aqueous layer basified (pH 11) with 1M sodium hydroxide solution. The mixture was filtered to remove tin salts and the ethyl acetate was separated, dried (MgSO4) and evaporated under reduced pressure to give the amine as a yellow oil (0.89 g, 99%).

Workup

  1. temperatureThe solution was cooled
  2. customthe solvent evaporated under reduced pressure
  3. customto give an off-white solid
  4. customThe solid was partitioned between water (50 mL) and ethyl actate (100 mL)
  5. filtrationThe mixture was filtered
  6. customto remove tin salts
  7. customthe ethyl acetate was separated
  8. dry with materialdried (MgSO4)
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-1ccb136593f145dfb1af562f856db190
Source dataset
uspto-grants-2007_01
Patent number
US07157585B2

Reaction notes

Loading…