Methanol → 6-(2-chloro-6-methoxy-pyridine-4-carbonyl)-4-methyl-3H-benzoxazol-2-one

HRID 469329Notes

Reaction equation

HRID 469329 reaction equation
[Na].Cl[C:3]1[CH:8]=[C:7]([C:9]([C:11]2[CH:20]=[C:19]([CH3:21])[C:14]3[NH:15][C:16](=[O:18])[O:17][C:13]=3[CH:12]=2)=[O:10])[CH:6]=[C:5]([Cl:22])[N:4]=1.[CH3:23][OH:24]>>[Cl:22][C:5]1[CH:6]=[C:7]([C:9]([C:11]2[CH:20]=[C:19]([CH3:21])[C:14]3[NH:15][C:16](=[O:18])[O:17][C:13]=3[CH:12]=2)=[O:10])[CH:8]=[C:3]([O:24][CH3:23])[N:4]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 5360545Sodium2×HCID 581812126-(2,6-dichloro-pyridine-4-carbonyl)-4-methyl-3H-benzoxazol-2-one

Product 1

HCID 581811586-(2-chloro-6-methoxy-pyridine-4-carbonyl)-4-methyl-3H-benzoxazol-2-one

Procedure

Under a nitrogen atmosphere 0.21 g (9.3 mmol) sodium were added batchwise to 50 mL MeOH. After the sodium had dissolved completely, 1.0 g (3.1 mmol) of 6-(2,6-dichloro-pyridine-4-carbonyl)-4-methyl-3H-benzoxazol-2-one were added and the mixture was refluxed for 5 h. Then the reaction mixture was evaporated down i. vac., the residue was combined with 50 mL water and the precipitated solid was suction filtered. This was washed with a little water and dried.

Workup

  1. temperaturethe mixture was refluxed for 5 h
  2. customThen the reaction mixture was evaporated down i
  3. filtrationfiltered
  4. washThis was washed with a little water
  5. customdried

Sources & evidence

ORD record
ord-22b04f9ed20c4ffcb824eee1b80c5705
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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