Aluminum(III) Chloride → 6-(5-bromo-pyridin-3-carbonyl)-4-methyl-3H-benzoxazol-2-one

HRID 469326Notes

Reaction equation

HRID 469326 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[N:5][CH:6]=[C:7]([CH:11]=1)[C:8](Cl)=[O:9].[CH3:12][C:13]1[C:18]2[NH:19][C:20](=[O:22])[O:21][C:17]=2[CH:16]=[CH:15][CH:14]=1.[Cl-].[Cl-].[Cl-].[Al+3]>>[Br:2][C:3]1[CH:11]=[C:7]([C:8]([C:15]2[CH:14]=[C:13]([CH3:12])[C:18]3[NH:19][C:20](=[O:22])[O:21][C:17]=3[CH:16]=2)=[O:9])[CH:6]=[N:5][CH:4]=1

Participants

4

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 127093364-Methyl-3H-benzooxazol-2-oneHCID 189717365-Bromo-nicotinic acid chloride hydrochloride

Product 1

HCID 581811166-(5-bromo-pyridin-3-carbonyl)-4-methyl-3H-benzoxazol-2-one

Procedure

2.57 g (10.0 mmol) 5-bromo-nicotinic acid chloride hydrochloride, 1.49 g (10.0 mmol) 4-methyl-3H-benzoxazol-2-one and 5.33 g (40.0 mmol) aluminium trichloride were heated to 125° C. with stirring for 1.5 h. After cooling to RT the mixture was mixed with ice water. The precipitate formed was suction filtered, washed with water and dried i. vac.

Workup

  1. customThe precipitate formed
  2. filtrationfiltered
  3. washwashed with water
  4. customdried i

Sources & evidence

ORD record
ord-708df34646e244ee8b57dd9f0e41748c
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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