m-Chloroperbenzoic acid → 3-Chlorobenzoic Acid

HRID 1819463Notes

Reaction equation

HRID 1819463 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)(C)(C)C.[Cl:16][C:17]1[CH:18]=[C:19]([CH:24]=[CH:25][CH:26]=1)[C:20]([O:22]O)=[O:21]>CCO>[CH:13]1[CH:12]=[N+:11]([O-:21])[CH:10]=[C:9]([CH2:8][NH2:7])[CH:14]=1.[Cl:16][C:17]1[CH:18]=[C:19]([CH:24]=[CH:25][CH:26]=1)[C:20]([OH:22])=[O:21]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 13948280tert-Butyl (pyridin-3-ylmethyl)carbamate

Product 2

HCID 4473-Chlorobenzoic AcidHCID 2985101-(1-Oxo-1lambda~5~-pyridin-3-yl)methanamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

To pyridin-3-ylmethyl-carbamic acid tert-butyl ester (3.89 g, 18.7 mmol) dissolved in EtOH (50 mL), was added 3-chloroperoxybenzoic acid (4.7 g, 27.4 mmol). After 4 hours the volatiles were removed in vacuo and the crude was redissolved in CH2Cl2 (25 mL). To this solution was added TFA (25 mL) and the reaction was stirred at 25° C. for 2 h then the volatiles were removed in vacuo. The crude was redissolved in CH2Cl2 and evaporated. This procedure was done twice more. (1-Oxy-pyridin-3-yl)-methylamine was obtained with contamination of 3-chlorobenzoic acid, but carried further without any additional purification (2.74 g).

Workup

  1. customAfter 4 hours the volatiles were removed in vacuo
  2. dissolutionthe crude was redissolved in CH2Cl2 (25 mL)
  3. additionTo this solution was added TFA (25 mL)
  4. customthe volatiles were removed in vacuo
  5. dissolutionThe crude was redissolved in CH2Cl2
  6. customevaporated

Sources & evidence

ORD record
ord-aeff01c2c8bf433d8d1819f7576bf421
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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