Acetonitrile → HCID 14075351, compound

HRID 2107911Notes

Reaction equation

HRID 2107911 reaction equation
[Br:1]Br.Cl.[CH3:4][N:5]1[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:14][C:13](=[O:22])[C:7]([C:8]([O:10]CC)=[O:9])=[C:6]1[CH3:23].CC#N>CO.O>[Br:1][C:14]1[C:13](=[O:22])[C:7]([C:8]([OH:10])=[O:9])=[C:6]([CH3:23])[N:5]([CH3:4])[C:15]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 24408BromineHCID 14075319HCID 14075319, compound

Product 1

HCID 14075351HCID 14075351, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

2.0 g (0.0125 mol) of bromine dissolved in 50 ml. of methanol is added dropwise over a 15 min. period to a solution of 2.7 g (0.00877 mol) ethyl 1,2-dimethyl-6-phenyl-4-oxonicotinate hydrochloride (Example 2) in 15 ml of methanol and 15 ml of water. The suspension formed is vacuum filtered and the filter cake, a yellow solid, is suspended in 60 g of 5% aqueous sodium hydroxide. The mixture is stirred and heated at 85° C. for 21/2 hrs. and is acidified with hydrochloric acid. The suspension formed is vacuum filtered to afford 2.4 g (85% yield) of 5-bromo-1,2-dimethyl-6-phenyl-4-oxonicotinic acid, mp 257°-258° C. (CH3CN).

Workup

  1. customThe suspension formed
  2. filtrationfiltered
  3. customThe suspension formed
  4. filtrationfiltered

Sources & evidence

ORD record
ord-1010f8df5fbe469eb94b59417f15b015
Source dataset
uspto-grants-1990_06
Patent number
US04936904

Reaction notes

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