Stannous chloride dihydrate → HCID 10631005, compound

HRID 343807Notes

Reaction equation

HRID 343807 reaction equation
[Cl:1][C:2]1[C:3]([CH2:12][CH3:13])=[CH:4][C:5]([N+:9]([O-])=O)=[C:6]([CH:8]=1)[NH2:7].O.O.[Sn](Cl)Cl>C(OCC)(=O)C>[NH2:9][C:5]1[CH:4]=[C:3]([CH2:12][CH3:13])[C:2]([Cl:1])=[CH:8][C:6]=1[NH2:7]

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 21189944HCID 21189944, compound

Product 1

HCID 10631005HCID 10631005, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-chloro-4-ethyl-2-nitroaniline (supplied by the Sigma-Aldrich Library of Rare Chemicals, 2.62 g, 13.1 mmol), tin (II) chloride dihydrate (14.7 g, 65.3 mmol) and ethyl acetate (130 ml) was heated under reflux for 22h. The mixture was cooled and partitioned between 1M aqueous sodium hydroxide (500 ml) and ethyl acetate (500 ml). The aqueous layer was extracted with ethyl acetate (250 ml), and the combined organic solutions were washed with saturated aqueous sodium chloride (100 ml), dried (MgSO4) and concentrated under reduced pressure to give 1,2-diamino4-chloro-5-ethylbenzene (2.70 g, >100%) as a white solid which was used directly without further purification.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 22h
  3. temperatureThe mixture was cooled
  4. custompartitioned between 1M aqueous sodium hydroxide (500 ml) and ethyl acetate (500 ml)
  5. extractionThe aqueous layer was extracted with ethyl acetate (250 ml)
  6. washthe combined organic solutions were washed with saturated aqueous sodium chloride (100 ml)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fc7d7b96432d4b64bc96fd5b5bb115dc
Source dataset
uspto-grants-1999_01
Patent number
US05863917

Reaction notes

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