Stannous chloride dihydrate → [4-Amino-2-(2-methylphenyl)benzoyl]methionine methyl ester

HRID 2121236Notes

Reaction equation

HRID 2121236 reaction equation
[CH3:1][O:2][C:3](=[O:28])[C@H:4]([CH2:24][CH2:25][S:26][CH3:27])[NH:5][C:6](=[O:23])[C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][C:8]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH3:22].O.O.Cl[Sn]Cl.C([O-])(O)=O.[Na+]>C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:28])[C@H:4]([CH2:24][CH2:25][S:26][CH3:27])[NH:5][C:6](=[O:23])[C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:8]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH3:22]

Participants

5

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 53719134[4-Nitro-2-(2-methylphenyl)benzoyl]methionine methyl ester

Product 1

HCID 20622819[4-Amino-2-(2-methylphenyl)benzoyl]methionine methyl esterYield 52%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the product of Example 308B (940 mg, 2.33 mmol) in ethyl acetate (50 mL) was added SnCl2.2H2O (1.85 g, 8.18 mmol) and the reaction was heated at reflux for 1 hour. The reaction mixture was cooled and basified to pH8 gradually with solid NaHCO3, stirred overnight, and extracted with ethyl acetate. The ethyl acetate extract was concentrated and the residue was purified by chromatography on silica gel (5% methanol-ethyl acetate) to give the aniline (450 mg, 52%) as an oil.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 1 hour
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted with ethyl acetate
  5. extractionThe ethyl acetate extract
  6. concentrationwas concentrated
  7. customthe residue was purified by chromatography on silica gel (5% methanol-ethyl acetate)

Sources & evidence

ORD record
ord-78e5abcb0a4348a3a0c22b0f835b9b88
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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