Potassium Carbonate → HCID 118389362, compound

HRID 925125Notes

Reaction equation

HRID 925125 reaction equation
[OH:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([C:10]2([C:14]#[N:15])[CH2:13][CH2:12][CH2:11]2)=[C:4]([N+:16]([O-:18])=[O:17])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:25][CH2:26][CH2:27][CH2:28]I>CC#N>[Cl:25][CH2:26][CH2:27][CH2:28][O:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([C:10]2([C:14]#[N:15])[CH2:11][CH2:12][CH2:13]2)=[C:4]([N+:16]([O-:18])=[O:17])[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 813631-Chloro-3-iodopropaneHCID 921351291-(4-Hydroxy-5-methoxy-2-nitrophenyl)cyclobutanecarbonitrile

Product 1

HCID 118389362HCID 118389362, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

1-(4-(Hydroxyl)-5-methoxy-2-nitrophenyl)cyclobutanecarbonitrile (0.5 g, 2 mmol) in MeCN (10 mL) was treated with potassium carbonate (0.306 g, 2.2 mmol) and 1-chloro-3-iodopropane (0.425 mL, 4 mmol) and stirred at 80° C. for 3 hours. The reaction mixture was concentrated, extracted with dichloromethane and washed with brine. The organic layer was dried (MgSO4), filtered and concentrated. Purification by flash chromatography (silica gel, 5-24% EtOAc/hexane) afforded 0.63 g (96%) of 1-(4-(3-chloropropoxy)-5-methoxy-2-nitrophenyl)cyclobutanecarbonitrile. MS (ESI) m/z 325 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionextracted with dichloromethane
  3. washwashed with brine
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash chromatography (silica gel, 5-24% EtOAc/hexane)

Sources & evidence

ORD record
ord-6672941f5a8a49e68bbf94631b4cd77c
Source dataset
uspto-grants-2016_03
Patent number
US09284272B2

Reaction notes

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