Sodium Hydroxide → 6-(Fluoromethyl)pyridin-2-amine

HRID 2244401Notes

Reaction equation

HRID 2244401 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][F:15])[N:9]=1)(C)(C)C.[OH-].[Na+]>Cl>[F:15][CH2:14][C:10]1[N:9]=[C:8]([NH2:7])[CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58674941HCID 58674941, compound

Product 1

HCID 552855066-(Fluoromethyl)pyridin-2-amineYield 78%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of (6-fluoromethyl-pyridin-2-yl)-carbamic acid tert-butyl ester (0.10 g, 0.43 mmol) in 6N HCl (2.00 ml) was warmed to 100° C. and stirred for 6 h. The clear solution was then cooled to room temperature and neutralized with 5N NaOH. The aqueousaqueous phase was extracted several times with dichloromethane. The combined organic phases were dried over sodium sulfate and evaporated to yield 6-fluoromethyl-pyridin-2-ylamine (0.04 g, 78%) as colorless oil, which was used crude.

Workup

  1. extractionThe aqueousaqueous phase was extracted several times with dichloromethane
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-a6a40b2f4c714cb1bbc0bd80d7a98311
Source dataset
uspto-grants-2010_03
Patent number
US07678815B2

Reaction notes

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