Water → HCID 18950361, compound

HRID 1492395Notes

Reaction equation

HRID 1492395 reaction equation
[NH2:1][C:2]1[C:3]([CH2:14]SC)=[C:4]([CH:10]=[CH:11][C:12]=1[Cl:13])[C:5]([O:7][CH2:8][CH3:9])=[O:6].O>C(O)C.[Ni]>[NH2:1][C:2]1[C:3]([CH3:14])=[C:4]([CH:10]=[CH:11][C:12]=1[Cl:13])[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

5

Reactant 2

HCID 962WaterHCID 18950256HCID 18950256, compound

Product 1

HCID 18950361HCID 18950361, compoundYield 72.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalyst2×HCID 702EthanolSolvent2×

Procedure

A solution of ethyl 3-amino-4-chloro-2-(methylsulphenylmethyl)benzoate (50 g) in ethanol was added to a stirred suspension of Raney Nickel (300 g) in ethanol. After stirring overnight at room temperature, a further addition of Raney Nickel was made and the mixture stirred for 2 hours. Water was added, the mixture filtered and the residue washed with dichloromethane. The filtrate was evaporated, re-extracted with ethyl acetate, dried (magnesium sulphate) and evaporated to give ethyl 3-amino-4-chloro-2-methylbenzoate (29.7 g) as a brown oil, NMR (CDCl3) 1.25 (t,3H), 2.25 (s,3H), 4.3 (q,2H), 7.05 (m,2H).

Workup

  1. stirringthe mixture stirred for 2 hours
  2. filtrationthe mixture filtered
  3. washthe residue washed with dichloromethane
  4. customThe filtrate was evaporated
  5. extractionre-extracted with ethyl acetate
  6. dry with materialdried (magnesium sulphate)
  7. customevaporated

Sources & evidence

ORD record
ord-a18bbe9fbd99489f8cc19d849460e565
Source dataset
uspto-grants-1994_12
Patent number
US05374606

Reaction notes

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