Sodium Hydroxide → HCID 12790120, compound

HRID 1579396Notes

Reaction equation

HRID 1579396 reaction equation
BrBr.[OH-:3].[Na+].[C:5]([C:8]1[CH:9]=[CH:10][C:11]2[O:20][C:15]3=[N:16][CH:17]=[CH:18][CH:19]=[C:14]3[C:13]([CH3:22])([CH3:21])[C:12]=2[CH:23]=1)(=[O:7])C>O.O1CCOCC1>[CH3:21][C:13]1([CH3:22])[C:14]2[C:15](=[N:16][CH:17]=[CH:18][CH:19]=2)[O:20][C:11]2[CH:10]=[CH:9][C:8]([C:5]([OH:7])=[O:3])=[CH:23][C:12]1=2

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 24408BromineHCID 13175740HCID 13175740, compound

Product 1

HCID 12790120HCID 12790120, compoundYield 78.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

4.8 g of bromine is added dropwise to a solution of 3.3 g of sodium hydroxide in 28 ml of water at below 0°C, and the mixture is allowed to stand at 0°C for 15 minutes. To the mixture is added dropwise and slowly a solution of 2.4 g of 7-acetyl-5,5-dimethyl-5H-[1]benzopyrano[2,3-b]pyridine in 10 ml of dioxane. The whole mixture is allowed to stand at room temperature for 2 hours, and then the solvent is removed by distillation under reduced pressure. To the residue are added water and benzene, and the mixture is warmed to 30°-40°C. The aqueous layer is neutralized with hydrochloric acid. The crystalline precipitate is recrystallized from aqueous acetic acid to give 1.9 g of 5,5-dimethyl-5H-[1]benzopyrano[2,3-b]pyridine-7-carboxylic acid melting at 241°-242°C.

Workup

  1. additionTo the mixture is added dropwise
  2. waitto stand at room temperature for 2 hours
  3. customthe solvent is removed by distillation under reduced pressure
  4. additionTo the residue are added water and benzene
  5. temperaturethe mixture is warmed to 30°-40°C
  6. customThe crystalline precipitate is recrystallized from aqueous acetic acid

Sources & evidence

ORD record
ord-bf28841760744cf69f74a220b325b94b
Source dataset
uspto-grants-1976_01
Patent number
US03931199

Reaction notes

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