Pyridine → HCID 54535103, compound

HRID 361629Notes

Reaction equation

HRID 361629 reaction equation
O[C:2]1([C:13]([O:15][CH3:16])=[O:14])[CH:10]=[C:9]2[C:4]([C:5]([CH3:12])=[CH:6][CH:7]=[C:8]2[CH3:11])=[N:3]1.N1C=CC=CC=1.[C:23](Cl)(=[O:25])[CH3:24].C1C[O:30]CC1>>[C:23]([O:25][N:3]1[C:4]2[C:9](=[C:8]([CH3:11])[CH:7]=[CH:6][C:5]=2[CH3:12])[CH:10]=[C:2]1[C:13]([O:15][CH3:16])=[O:14])(=[O:30])[CH3:24]

Participants

5

Reactant 4

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 8028TetrahydrofuranHCID 70346529HCID 70346529, compound

Product 1

HCID 54535103HCID 54535103, compoundYield 92%

Procedure

A solution of 0.3 g (1.37 mmol) of methyl 2-hydroxy-4,7-dimethylindole-2-carboxylate and 0.13 ml of pyridine in 20 ml of anhydrous THF was cooled, to 0° C. and 0.12 ml of acetyl chloride was gradually added dropwise. The reaction mixture was stirred for 1 hour and then added dropwise to ice water. The crystals were separated by filtration and dried under reduced pressure to provide 0.30 g of green crystals. Yield: 92%

Workup

  1. customThe crystals were separated by filtration
  2. customdried under reduced pressure

Sources & evidence

ORD record
ord-905670750fe14f2ebf3f9fc93a5c02b8
Source dataset
uspto-grants-1999_02
Patent number
US05866594

Reaction notes

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