Tin tetrachloride → Methyl 2-(4-amino-2-chlorophenyl)acetate

HRID 1004078Notes

Reaction equation

HRID 1004078 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][C:6]=1[Cl:14].[Sn](Cl)(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>CO>[CH3:1][O:2][C:3](=[O:15])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][C:6]=1[Cl:14]

Participants

5

Reactant 3

HCID 24287Tin tetrachlorideHCID 516892Sodium BicarbonateHCID 21876245Methyl 2-(2-chloro-4-nitrophenyl)acetate

Product 1

HCID 21876454Methyl 2-(4-amino-2-chlorophenyl)acetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(4 nitro-2-chlorophenyl )acetic acid methyl ester was reduced with tin chloride in methanol at reflux for 2 h. The solution was poured over ice and neutralized with saturated sodium bicarbonate. The mixture was extracted with methylene chloride, dried (MgSO4), and concentrated. The oil was purified by silica gel chromatography eluted with hexane/ethyl acetate(9:1 to 8:2) to yield the title compound (0.81 g).

Workup

  1. temperatureat reflux for 2 h
  2. extractionThe mixture was extracted with methylene chloride
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe oil was purified by silica gel chromatography
  6. washeluted with hexane/ethyl acetate(9:1 to 8:2)

Sources & evidence

ORD record
ord-85c9404c43e54cd9bde545dec99933d8
Source dataset
uspto-grants-2000_04
Patent number
US06048872

Reaction notes

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