Tin dichloride dihydrate → HCID 66777671, compound

HRID 878465Notes

Reaction equation

HRID 878465 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-c25a75f674414a67bd59d879b95d64f5
Source dataset
uspto-grants-2015_03
Patent number
US08987468B2

Reaction notes

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