Acetyl chloride → HCID 13175740, compound

HRID 1579389Notes

Reaction equation

HRID 1579389 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][C:6]1([CH3:20])[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[O:9][C:8]2[CH:16]=[CH:17][CH:18]=[CH:19][C:7]1=2.[C:21](Cl)(=[O:23])[CH3:22]>>[C:21]([C:18]1[CH:17]=[CH:16][C:8]2[O:9][C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:15]3[C:6]([CH3:20])([CH3:5])[C:7]=2[CH:19]=1)(=[O:23])[CH3:22]

Participants

4

Reactant 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 215684065H-[1]Benzopyrano[2,3-b]pyridine, 5,5-dimethyl-

Product 1

HCID 13175740HCID 13175740, compoundYield 66.7%

Procedure

9.5 g of powdered aluminum chloride is added in small portions to a mixture of 5 g of 5,5-dimethyl-5H-[1]benzopyrano[2,3-b]pyridine and 5.6 g of acetyl chloride, keeping the temperature at 20°-30°C. The mixture is allowed to stand at 80°C for 1.5 hours, and then poured into ice water. The mixture is extracted with benzene, and the extract is washed with water. The benzene is distilled off, and the crystalline residue is recrystallized from isopropyl ether containing a small amount of carbon tetrachloride to give 4 g of 7-acetyl-5,5-dimethyl-5H-[1]benzopyrano[2,3-b]pyridine melting at 106°-108°C.

Workup

  1. customat 20°-30°C
  2. extractionThe mixture is extracted with benzene
  3. washthe extract is washed with water
  4. distillationThe benzene is distilled off
  5. customthe crystalline residue is recrystallized from isopropyl ether containing a small amount of carbon tetrachloride

Sources & evidence

ORD record
ord-8892dbd8840347af82edc049c697c7c3
Source dataset
uspto-grants-1976_01
Patent number
US03931199

Reaction notes

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