Pyridine → 10-Acetamido-5,5-dimethyl-8-(1,2-dimethylheptyl)5H-[1]benzopyrano[4,3-c]pyridine

HRID 1763292Notes

Reaction equation

HRID 1763292 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6]1[C:11]2[C:12]3[CH:13]=[N:14][CH:15]=[CH:16][C:17]=3[C:18]([CH3:21])([CH3:20])[O:19][C:10]=2[CH:9]=[C:8]([CH:22]([CH3:30])[CH:23]([CH3:29])[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:7]=1.N1C=CC=CC=1>CCOCC>[C:1]([NH:5][C:6]1[C:11]2[C:12]3[CH:13]=[N:14][CH:15]=[CH:16][C:17]=3[C:18]([CH3:20])([CH3:21])[O:19][C:10]=2[CH:9]=[C:8]([CH:22]([CH3:30])[CH:23]([CH3:29])[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:7]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 2030973410-Amino-5,5-dimethyl-8-(1,2-dimethylheptyl)-5H-[1]benzopyrano[4,3-c]pyridine

Product 1

HCID 5443128910-Acetamido-5,5-dimethyl-8-(1,2-dimethylheptyl)5H-[1]benzopyrano[4,3-c]pyridine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Acetyl chloride (0.39 g., 5 mmole) was added to a stirred solution of 0.78 g. (2.2 mmole) of 10-amino-5,5-dimethyl-8-(1,2-dimethylheptyl)-5H-[1]benzopyrano[4,3-c]-pyridine in 10 ml. of dry pyridine, cooled in an ice bath. After stirring at room temperature for 18 hours, the mixture was poured into 100 ml. of ice water and exracted with ether. The ether extracts were washed with water, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was purified by chromatography on a Florisil column (60-100 mesh) and eluted with chloroform and then graded chloroform-methanol mixtures to give the pure product.

Workup

  1. additionthe mixture was poured into 100 ml
  2. washThe ether extracts were washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by chromatography on a Florisil column (60-100 mesh)
  6. washeluted with chloroform
  7. customto give the pure product

Sources & evidence

ORD record
ord-d81fa6805f174110b81ff91be75671e2
Source dataset
uspto-grants-1978_09
Patent number
US04111942

Reaction notes

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