Pentane → HCID 178487731, compound

HRID 1852098Notes

Reaction equation

HRID 1852098 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]=1[CH3:13])C.C([Li])(C)(C)C.CCCCC.[F:27][C:28]1[CH:35]=[CH:34]C(C#N)=[CH:30][CH:29]=1>C1COCC1>[F:27][C:28]1[CH:35]=[CH:34][C:16]([C:15]2[N:3]=[C:4]([OH:14])[C:5]3[C:6]([CH:13]=2)=[CH:7][C:8]([O:11][CH3:12])=[CH:9][CH:10]=3)=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 8003PentaneHCID 145174-FluorobenzonitrileHCID 11053218N,N-diethyl-4-methoxy-2-methyl-benzamideHCID 178418306HCID 178418306, compound

Product 1

HCID 178487731HCID 178487731, compoundYield 58%

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 (4.52 ml) at −78° C. was added dropwise tert-butyllithium 1.7 M in pentane (1.59 ml, 2.71 mmol) and the solution was stirred for 0.5 h before addition of 4-fluorobenzonitrile (274 mg, 2.259 mmol) in THF (4.52 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 3-(4-fluorophenyl)-6-methoxyisoquinolin-1-ol (350 mg, 58% 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-9f987cbc1b8e408e80f3cf1c6481e6f4
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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