Tetrahydrofuran → HCID 39104401, compound

HRID 1481679Notes

Reaction equation

HRID 1481679 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]#N)=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH2:3]1.[CH2:14]([Mg]Cl)[CH2:15][CH3:16].C1C[O:22]CC1>>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12](=[O:22])[CH2:14][CH2:15][CH3:16])=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH2:3]1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 620964851-Methyl-1,2,3,4-tetrahydroquinoline-6-carbonitrileHCID 178455855HCID 178455855, compound

Product 1

HCID 39104401HCID 39104401, compoundYield 51%

Conditions

Temperature
50 °C

Procedure

To a solution of 1-methyl-1,2,3,4-tetrahydroquinoline-6-carbonitrile (4.53 g, 26.3 mmol) in THF (30 mL) was added n-PrMgCl (2.0M in ether, 26.3 mL, 52.6 mmol, 2.0 eq) at room temperature. Then the mixture was heated to 50° C. and stirred overnight. The reaction was quenched with ice cold 1N HCl and stirred overnight. The biphasic mixture was extracted by CH2Cl2 (3×40 mL). The combined organic layers were dried over Na2SO4 then concentrated to give a crude product which was purified by flash column chromatography (0-25% EtOAc in hexanes) to afford the title compound (2.94 g, 13.5 mmol, 51%).

Workup

  1. customThe reaction was quenched with ice cold 1N HCl
  2. stirringstirred overnight
  3. extractionThe biphasic mixture was extracted by CH2Cl2 (3×40 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationthen concentrated
  6. customto give a crude product which
  7. customwas purified by flash column chromatography (0-25% EtOAc in hexanes)

Sources & evidence

ORD record
ord-f8df8083d1b24e35bc38a9611fd8e36b
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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