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

HRID 2171529Notes

Reaction equation

HRID 2171529 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 107A) are dissolved in 285 ml of 4N hydrogen chloride in dioxane and stirred for 30 min. The reaction mixture is concentrated to one half, and an equal portion of diethyl ether is added. The reaction mixture is stirred for 20 min and the product is filtered off and washed with diethyl ether. 11 g (94% of theory) of the product are obtained as a solid.

Workup

  1. concentrationThe reaction mixture is concentrated to one half
  2. additionan equal portion of diethyl ether is added
  3. stirringThe reaction mixture is stirred for 20 min
  4. filtrationthe product is filtered off
  5. washwashed with diethyl ether
  6. custom11 g (94% of theory) of the product are obtained as a solid

Sources & evidence

ORD record
ord-65af9683db9f4a0ea59c6b5fd108869c
Source dataset
uspto-grants-2015_06
Patent number
US09051323B2

Reaction notes

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