Ethyl bromoacetate → (3-Methyl-5-nitro-4-oxo-4H-quinolin-1-yl)-acetic acid ethyl ester

HRID 1948106Notes

Reaction equation

HRID 1948106 reaction equation
[CH3:1][C:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:13]([O-:15])=[O:14])[NH:4][CH:3]=1.CC1C(=O)C2C(=CC([N+]([O-])=O)=CC=2)NC=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40]>C1(C)C=CC=CC=1>[CH2:42]([O:41][C:39](=[O:40])[CH2:38][N:4]1[C:5]2[C:10](=[C:9]([N+:13]([O-:15])=[O:14])[CH:8]=[CH:7][CH:6]=2)[C:11](=[O:12])[C:2]([CH3:1])=[CH:3]1)[CH3:43]

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 105123693-methyl-5-nitroquinolin-4(1H)-oneHCID 105601023-methyl-7-nitroquinolin-4(1H)-one

Product 1

HCID 67256021(3-Methyl-5-nitro-4-oxo-4H-quinolin-1-yl)-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 3-methyl-5-nitroquinolin-4(1H)-one and 3-methyl-7-nitroquinolin-4(1H)-one (Eur. J. Med. Chem. 1997, 32, 547, 500 mg, 2.45 mmol,) and cesium carbonate (800 mg (2.45 mmol) in toluene (50 mL) was treated with ethyl bromoacetate (0.3 mL, 2.45 mmol) and stirred at RT for 3 days. The solid (Cesium salt of starting materials) was filtered and washed with dichloromethane. The filtrate was concentrated to give 400 mg of the crude material which was purified using flash column chromatography (DCM:MeOH, 99:1) to isolate the desired region-isomer: 100 mg 1H NMR (CDCl3, 300 MHz): δ 1.3 (m, 3H, J=7.2 Hz), 2.08 (s, 3H), 4.25 (q, 2H, J=7.2 Hz), 4.8 (s, 2H), 7.3 (m, 2H), 7.4 (s, 1H), 7.65 (t, J=8 Hz, 1H). The other isomer was also recovered: 70 mg.

Workup

  1. filtrationThe solid (Cesium salt of starting materials) was filtered
  2. washwashed with dichloromethane
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-edd0b8cef1ac46878e5c9e2053ab8732
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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