Tin dichloride dihydrate → HCID 66777671, compound

HRID 1048648Notes

Reaction equation

HRID 1048648 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:20])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])=[C:4]([N+:21]([O-])=O)[CH:3]=1.Cl[Sn]Cl.O>CCO>[NH2:21][C:4]1[CH:3]=[C:2]([Br:1])[CH:7]=[CH:6][C:5]=1[NH:8][C:9](=[O:20])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17]

Participants

4

Reactant 2

HCID 43835034Tin dichloride dihydrateHCID 66777974HCID 66777974, compound

Product 1

HCID 66777671HCID 66777671, compoundYield 66.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of methyl 8-(4-bromo-2-nitrophenylamino)-8-oxooctanoate (241 mg, 0.623 mmol) in EtOH was added SnCl2.H2O (490 mg, 2.37 mmol). The reaction was heated to reflux overnight and quenched by water. The mixture was filtered and the filtrate was extracted with ethyl acetate. The combined organic layer was dried, concentrated and purified by biotage column chromatography to afford methyl 8-(2-amino-4-bromophenylamino)-8-oxooctanoate (149 mg)

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux overnight
  3. customquenched by water
  4. filtrationThe mixture was filtered
  5. extractionthe filtrate was extracted with ethyl acetate
  6. customThe combined organic layer was dried
  7. concentrationconcentrated
  8. custompurified by biotage column chromatography

Sources & evidence

ORD record
ord-e6a044578442493aa7132664e56ccc35
Source dataset
uspto-grants-2016_07
Patent number
US09381196B2

Reaction notes

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