2-(5-Nitro-2-pyridinylthio)ethyl-3-chlorobenzoate → 2-[(5-Amino-2-pyridinyl)thio]ethyl-3-chlorobenzoate

HRID 731770Notes

Reaction equation

HRID 731770 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([S:10][CH2:11][CH2:12][O:13][C:14](=[O:22])[C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=2)=[N:8][CH:9]=1)([O-])=O>C1(C)C=CC=CC=1.CO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([S:10][CH2:11][CH2:12][O:13][C:14](=[O:22])[C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=2)=[N:8][CH:9]=1

Participants

5

Reactant 1

HCID 116242282-(5-Nitro-2-pyridinylthio)ethyl-3-chlorobenzoate

Product 1

HCID 578381082-[(5-Amino-2-pyridinyl)thio]ethyl-3-chlorobenzoate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

A mixture of 2-[(5-nitro-2-pyridinyl)thio]ethyl 3-chlorobenzoate (5) (0.24 g, 0.71 mmol) and 10% Pd/C (0.10 g) in toluene or methanol was agitated under a hydrogen atmosphere (40 PSI) for 1 h. The reaction mixture was filtered through Celite® and concentrated to give 2-[(5-amino-2-pyridinyl)thio]ethyl-3-chlorobenzoate (51), LCMS: purity: 99%; MS (m/e): 309 (MH+), which was used without further purification. Acetyl chloride (4.6 μL, 0.064 mmol) was added to a room temperature solution of 2-[(5-amino-2-pyridinyl)thio]ethyl-3-chlorobenzoate (51) (18.9 mg, 0.061 mmol) and triethylamine (18 μL, 0.13 mmol) in anhydrous dichloromethane (1.0 mL), After 16 h, the reaction mixture was diluted with dichloromethane and washed with 1N HCl and brine and then dried over anhydrous MgSO4. Purification by silica gel chromatography provided 2-[(5-acetylamino-2-pyridinyl)thio]ethyl-3-chlorobenzoate (52), LCMS: purity: 99%; MS (m/e): 351 (MH+).

Workup

  1. filtrationThe reaction mixture was filtered through Celite®
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-9474ec8b5e9849179ba06317dec92d13
Source dataset
uspto-grants-2009_09
Patent number
US07585883B2

Reaction notes

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