tert-Butyl{6-chloro-3-[(hydroxyimino)methyl]pyridin-2-yl}carbamate → 2-Amino-6-chloropyridine-3-carbaldehyde oxime hydrochloride

HRID 444830Notes

Reaction equation

HRID 444830 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8]C(=O)OC(C)(C)C)[C:5]([CH:16]=[N:17][OH:18])=[CH:4][CH:3]=1>Cl.O1CCOCC1>[ClH:1].[NH2:8][C:6]1[C:5]([CH:16]=[N:17][OH:18])=[CH:4][CH:3]=[C:2]([Cl:1])[N:7]=1

Participants

4

Reactant 1

HCID 76639260tert-Butyl{6-chloro-3-[(hydroxyimino)methyl]pyridin-2-yl}carbamate

Product 1

HCID 866350212-Amino-6-chloropyridine-3-carbaldehyde oxime hydrochloride

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

15.5 g (57 mmol) of tert-butyl {6-chloro-3-[(hydroxyimino)methyl]pyridin-2-yl}carbamate (Example 26A) were dissolved in 285 ml of 4N hydrogen chloride in dioxane and the mixture was stirred for 30 min. The reaction mixture was concentrated to half of its original volume and the same amount of diethyl ether was added. The reaction mixture was stirred for 20 min and the product was filtered off and washed with diethyl ether. This gave 11 g (94% of theory) of the product as a solid.

Workup

  1. concentrationThe reaction mixture was concentrated to half of its original volume
  2. additionthe same amount of diethyl ether was added
  3. stirringThe reaction mixture was stirred for 20 min
  4. filtrationthe product was filtered off
  5. washwashed with diethyl ether

Sources & evidence

ORD record
ord-e8f895acf1e04606b4387f9a01d3c98d
Source dataset
uspto-grants-2013_07
Patent number
US08476267B2

Reaction notes

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