Phosphorus oxychloride → 1422469-43-9

HRID 1497415Notes

Reaction equation

HRID 1497415 reaction equation
P(Cl)(Cl)([Cl:3])=O.O[C:7]1[N:12]=[C:11]2[C:13]([CH3:17])([CH3:16])[CH2:14][CH2:15][C:10]2=[CH:9][C:8]=1[C:18]#[N:19]>>[Cl:3][C:7]1[N:12]=[C:11]2[C:13]([CH3:17])([CH3:16])[CH2:14][CH2:15][C:10]2=[CH:9][C:8]=1[C:18]#[N:19]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178423777HCID 178423777, compound

Product 1

HCID 798578191422469-43-9Yield 78.8%

Conditions

Temperature
27.5 °C

Procedure

Phosphorous oxychloride (1.9 mL, 24 mmol) was added to 2-hydroxy-7,7-dimethyl-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carbonitrile (0.8 g, 4.3 mmol), obtained in step-1, at 0° C. over a period of about 10 min. The mixture was warmed to a temperature of about 20-35° C. and was heated further to about 80° C. The mixture was stirred at about 80° C. for about 18 h. The reaction mixture was cooled to a temperature of about 20-35° C. and then was poured into crushed ice. The solid which separated out was filtered off and dried under reduced pressure to get 2-chloro-7,7-dimethyl-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carbonitrile (0.7 g).

Workup

  1. customobtained in step-1, at 0° C. over a period of about 10 min
  2. temperaturewas heated further to about 80° C
  3. temperatureThe reaction mixture was cooled to a temperature of about 20-35° C.
  4. additionwas poured
  5. custominto crushed ice
  6. customThe solid which separated out
  7. filtrationwas filtered off
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-f3c9392596654b08abf9e0d9421736fe
Source dataset
uspto-grants-2015_12
Patent number
US09199967B2

Reaction notes

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