Water → HCID 23533344, compound

HRID 2414504Notes

Reaction equation

HRID 2414504 reaction equation
[CH3:1][O:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([C:13](=[O:15])[CH:14]=1)=[CH:11][C:10]([O:16][CH3:17])=[CH:9][C:8]=2[Br:18])=[O:4].[H-].[Na+].[CH3:21][Si:22]([CH3:29])([CH3:28])[CH2:23][CH2:24][O:25][CH2:26]Cl.O>CN1C(=O)CCC1>[CH3:1][O:2][C:3]([C:5]1[CH:14]=[C:13]([O:15][CH2:26][O:25][CH2:24][CH2:23][Si:22]([CH3:29])([CH3:28])[CH3:21])[C:12]2[C:7](=[C:8]([Br:18])[CH:9]=[C:10]([O:16][CH3:17])[CH:11]=2)[N:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 69268420HCID 69268420, compound

Product 1

HCID 23533344HCID 23533344, compoundYield 101.5%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A brown solution of 8-bromo-6-methoxy-4-oxo-1,4-dihydro-quinoline-2-carboxylic acid methyl ester (6.73 g, 21.6 mmol) in 100 mL N-methyl pyrolidinone was treated with sodium hydride (60% dispersion in oil, 1.028 g, 25.7 mmol). Gas evolution and warming were observed. The reaction was stirred for 10 minutes at room temperature under nitrogen. Addition of 2-(trimethylsilyl)ethoxymethyl chloride (5.00 mL, 28.3 mmol) resulted in a slightly cloudy, light brown solution. After 2.5 hours at room temperature, the reaction mixture was poured into 800 mL water and stirred for 15 minutes. The resulting cream colored precipitate was isolated by filtration, washed with water, and dried under high vacuum to afford the product as a cream colored solid (9.70 g, quantitative yield). 1H NMR (300 MHz, DMSO, d6) δ 7.976 (d, 1H, Jm=2.7 Hz, ArH7), 7.79 (s, 1H, C═CH), 7.53 (d, 1H, Jm=2.7 Hz, ArH5), 5.70 (s, 2H, OCH2O), 3.99 (s, 6H, OCH3 and CO2CH), 3.88 (t, 2H, J=8.0 Hz, OCH2CH2Si), 0.97 (t, 2H, J=8.0 Hz, OCH2CH2Si), −0.04 (s, 9H, Si(CH3)3; Mass Spec.: calc. for [C18H24BrNO5Si+H]+ Theor. m/z=442, 444; Obs. 442, 444.

Workup

  1. temperatureGas evolution and warming
  2. customresulted in a slightly cloudy, light brown solution
  3. waitAfter 2.5 hours at room temperature
  4. stirringstirred for 15 minutes
  5. customThe resulting cream colored precipitate was isolated by filtration
  6. washwashed with water
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-02ca589fc6fc456d9c03a1c7c6d392f3
Source dataset
uspto-grants-2004_11
Patent number
US06812225B2

Reaction notes

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