3-(Chloromethyl)pyridine → HCID 22320205, compound

HRID 498005

Reaction equation

HRID 498005 reaction equation
O=[C:2]([CH3:15])[CH2:3][C:4]1[O:9][C:8](=[O:10])[C:7]2[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=2[N:5]=1.[NH:16]([CH2:18][C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1)[NH2:17].ClCC1C=NC=CC=1>C(O)C>[CH3:15][C:2]1[CH:3]=[C:4]([NH:5][C:6]2[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=2[C:8]([OH:9])=[O:10])[N:16]([CH2:18][C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[N:17]=1

Participants

5

Reactant 3

HCID 183583-(Chloromethyl)pyridineHCID 12232495Pyridin-3-ylmethyl-hydrazineHCID 159380972-(2-Oxo-propyl)-benzo[D][1,3]oxazin-4-one

Product 1

HCID 22320205HCID 22320205, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution in ethanol (50 mL) of 2-(2-oxopropyl)-4H-3,1-benzoxazin-4-one (11.2 g, 55.1 mmol) and 3-hydrazinomethylpyridine (7.44 g, 60.4 mmol) which was prepared from 3-chloromethylpyridine following the method described in Reference Example 2-2, was heated under reflux for 1 hour. The solution was cooled to room temperature, and the resulting crude crystals were collected by filtration. The crystals were washed with ethanol and air dried to give the title compound (11.3 g, 67% yield). mp: 180-183° C. (recrystallized from ethanol).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hour
  3. filtrationthe resulting crude crystals were collected by filtration
  4. washThe crystals were washed with ethanol and air
  5. customdried

Sources & evidence

ORD record
ord-cf44457fb6344e3fba6132667320dab9
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Linked notes

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