1,4-Dioxane hydrochloride → 6-Chloro-4-iodopyridin-3-amine

HRID 859773Notes

Reaction equation

HRID 859773 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:9]=[N:10][C:11]([Cl:15])=[CH:12][C:13]=1[I:14])(C)(C)C.Cl.O1CCOCC1>C(Cl)Cl>[Cl:15][C:11]1[N:10]=[CH:9][C:8]([NH2:7])=[C:13]([I:14])[CH:12]=1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 53415320tert-Butyl (6-chloro-4-iodopyridin-3-yl)carbamate

Product 1

HCID 184070406-Chloro-4-iodopyridin-3-amineYield 100.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of (6-chloro-4-iodo-pyridin-3-yl)-carbamic acid tert-butyl ester (8.6 g, 24.3 mmol) dissolved in CH2Cl2 was treated with 4 N HCl/dioxane (100 mL) and stirred at room temperature for 2 hours. The reaction mixture was diluted with CH2Cl2 and washed with 2 N NaOH. The organic layer was dried over MgSO4 and concentrated to give the product as a solid (6.2 g, 100%).

Workup

  1. washwashed with 2 N NaOH
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e4bd85ce45d9448dbba09bdbf9bb4c5b
Source dataset
uspto-grants-2006_12
Patent number
US07151105B2

Reaction notes

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