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

HRID 1644306Notes

Reaction equation

HRID 1644306 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 22226298MeOH ACN DCMSolvent

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-fd0475daf6ce4ebc919041f7788a1bc1
Source dataset
uspto-grants-2012_02
Patent number
US08124602B2

Reaction notes

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