1H-Pyrrolo[2,3-b]pyridine, 2,3-dihydro-1,3,3-trimethyl-2-methylene- → HCID 15100094, compound

HRID 704306Notes

Reaction equation

HRID 704306 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][N:9]=2)[C:4]([CH3:12])([CH3:11])[C:3]1=[CH2:13].[N:14]([C:16]1[C:21]([O:22][CH3:23])=[CH:20][C:19]([O:24][CH3:25])=[CH:18][C:17]=1[OH:26])=O>C(O)C.CCOCC>[CH3:1][N:2]1[C:10]2=[N:9][CH:8]=[CH:7][CH:6]=[C:5]2[C:4]([CH3:11])([CH3:12])[C:3]21[CH:13]=[N:14][C:16]1[C:21]([O:22][CH3:23])=[CH:20][C:19]([O:24][CH3:25])=[CH:18][C:17]=1[O:26]2

Participants

5

Reactant 2

HCID 1705131H-Pyrrolo[2,3-b]pyridine, 2,3-dihydro-1,3,3-trimethyl-2-methylene-HCID 144192703,5-Dimethoxy-2-nitrosophenol

Product 1

HCID 15100094HCID 15100094, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

Into a three-necked 100 milliliter round bottom flask was charged a solution of 0.8 grams of the thus prepared 1,3,3-trimethyl-2-methylene-1,7-diazaindane in 20 milliliters of absolute ethanol. The solution was heated under a nitrogen pad to 60°-65° C. and 0.84 grams of 2-nitroso-3,5-dimethoxyphenol added to the flask. The reaction mixture was maintained at temperature and refluxing for a total reaction time of about 26 hours. The ethanol was removed on a rotary evaporator and the resulting reaction mixture taken up in ether and filtered. The ether solution sequentially was washed with 100 milliliters of a 10 percent sodium hydroxide solution, and 100 milliliters of a saturated sodium chloride solution and then dried over potassium carbonate. The ether was removed under vacuum. A silica gel column was used to isolate the final product, i.e., 1',3'-Dihydro-1',3',3'-trimethyl-5,7-dimethoxyspiro-[2H-1,4-benzoxazine-2,2'-[2H] pyrrolo[2,3-b]pyridine]. Identification of the product was confirmed by appropriate spectral analysis.

Workup

  1. temperatureThe solution was heated under a nitrogen pad to 60°-65° C.
  2. temperatureThe reaction mixture was maintained at temperature
  3. temperaturerefluxing for a total reaction time of about 26 hours
  4. customThe ethanol was removed on a rotary evaporator
  5. customthe resulting reaction mixture
  6. filtrationfiltered
  7. washThe ether solution sequentially was washed with 100 milliliters of a 10 percent sodium hydroxide solution, and 100 milliliters of a saturated sodium chloride solution
  8. dry with materialdried over potassium carbonate
  9. customThe ether was removed under vacuum

Sources & evidence

ORD record
ord-e0bc184219814d06869d48ae1b1454a8
Source dataset
uspto-grants-1991_01
Patent number
US04986934

Reaction notes

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