Water → HCID 23533344, compound

HRID 1181963Notes

Reaction equation

HRID 1181963 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>CN1CCCC1=O>[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-methylpyrolidinone 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, 1 H, Jm=2.7 Hz, ArH7), 7.79 (s, 1 H, C═CH), 7.53 (d, 1 H, Jm=2.7 Hz, ArH5), 5.70 (s, 2 H, OCH2O), 3.99 (s, 6 H, OCH3 and CO2CH3), 3.88 (t, 2 H, J=8.0 Hz, OCH2CH2Si), 0.97 (t, 2 H, J=8.0 Hz, OCH2CH2Si), ), −0.04 (s, 9 H, Si(C H3)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-6d9f74a578874b569f869331b193f35e
Source dataset
uspto-grants-2007_10
Patent number
US07285662B2

Reaction notes

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