Triethylamine → 7-Methoxy-3,4-dihydroquinolin-2(1H)-one

HRID 255185Notes

Reaction equation

HRID 255185 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1.[CH2:13](N(CC)CC)C.C[Si](C=[N+]=[N-])(C)C>ClCCl.CO.C(#N)C>[CH3:13][O:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 167693TrimethylsilyldiazomethaneHCID 27857587-Hydroxy-3,4-dihydrocarbostyril

Product 1

HCID 128994187-Methoxy-3,4-dihydroquinolin-2(1H)-oneYield 73%

Reagents, catalysts & solvents 1

HCID 22226298HCID 22226298, compoundSolvent

Procedure

A mixture of 7-hydroxy-3,4-dihydroquinolin-2(1H)-one (3.0 g, 17 mmol) and triethyl amine (3.14 mL, 22 mmol) in dichloromethane/methanol/acetonitrile (10:1:10, 168 mL) was treated with (trimethylsilyl)diazomethane (2M solution in hexanes, 10.25 mL, 20.5 mmol). It was stirred over night at room temperature, the solvent was removed under reduced pressure and chromatography on silica gel with hexanes/acetone (1:1) gave 2.2 g (67%) of the product as a colorless solid.

Workup

  1. customthe solvent was removed under reduced pressure and chromatography on silica gel with hexanes/acetone (1:1)

Sources & evidence

ORD record
ord-ce70ae46bc034020b05d60f45d7f6552
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Reaction notes

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