Pentane → HCID 178487762, compound

HRID 1852100Notes

Reaction equation

HRID 1852100 reaction equation
C([N:3]([CH2:15][CH3:16])[C:4](=[O:14])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:6]=1C)C.C([Li])(C)(C)C.CCCCC.[N:27]1(C#N)[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1>C1COCC1>[CH3:12][O:11][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[C:4]([OH:14])=[N:3][C:15]([N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1)=[CH:16]2

Participants

6

Reactant 4

HCID 8003PentaneHCID 737384-MorpholinecarbonitrileHCID 11053218N,N-diethyl-4-methoxy-2-methyl-benzamideHCID 178418306HCID 178418306, compound

Product 1

HCID 178487762HCID 178487762, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of N,N-diethyl-4-methoxy-2-methylbenzamide (500 mg, 2.259 mmol) in THF (5 ml) at −78° C. was added dropwise tert-butyllithium 1.7 M in pentane (2658 μl, 4.52 mmol) and the solution was stirred for 0.5 h before addition of morpholine-4-carbonitrile (253 mg, 2.259 mmol) in THF (5 ml). The resulting solution was warmed to rt and stirred for 16 h. The reaction mixture was quenched with water, neutralized with 1 N HCl. The precipitated solid was collected and washed with water to give 6-methoxy-3-morpholinoisoquinolin-1-ol (350 mg, 60% yield) as a solid after drying.

Workup

  1. customThe reaction mixture was quenched with water
  2. customThe precipitated solid was collected
  3. washwashed with water

Sources & evidence

ORD record
ord-62a57e66bcb94052b134de67501faf6c
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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