Pentane → HCID 178487737, compound

HRID 1852093Notes

Reaction equation

HRID 1852093 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.[Cl:27][C:28]1[CH:29]=C([CH:33]=[CH:34][C:35]=1[O:36][CH3:37])C#N>C1COCC1>[Cl:27][C:28]1[CH:29]=[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:33]=[CH:34][C:35]=1[O:36][CH3:37]

Participants

6

Reactant 4

HCID 8003PentaneHCID 43231053-Chloro-4-methoxybenzonitrileHCID 11053218N,N-diethyl-4-methoxy-2-methyl-benzamideHCID 178418306HCID 178418306, compound

Product 1

HCID 178487737HCID 178487737, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of N,N-diethyl-4-methoxy-2-methylbenzamide (1 g, 4.52 mmol) in THF (9 ml) at −78° C. was added dropwise tert-butyllithium 1.7 M in pentane (3.19 ml, 5.42 mmol) and the solution was stirred for 0.5 h before addition of 3-chloro-4-methoxybenzonitrile (0.757 g, 4.52 mmol) in THF (9 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-(3-chloro-4-methoxyphenyl)-6-methoxyisoquinolin-1-ol (1.2 g, 84% yield) as a solid after drying. MS: MS m/z 316.1 (M++1).

Workup

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

Sources & evidence

ORD record
ord-9e790aa999594929bb1f3fd0e1ebdc0b
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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