Methanol → HCID 86588219, compound

HRID 1814322Notes

Reaction equation

HRID 1814322 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2C(=O)C=[N+]=[N-])[N:3]=1.CO.[C:19]([O:22][CH2:23]C)(=[O:21])[CH3:20]>C(N(CC)CC)C.C([O-])(=O)C1C=CC=CC=1.[Ag+]>[CH3:23][O:22][C:19](=[O:21])[CH2:20][C:8]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:9]=1[CH:10]=[CH:11][C:2]([Cl:1])=[N:3]2

Participants

6

Reactant 3

HCID 887MethanolHCID 8857Ethyl AcetateHCID 73979837HCID 73979837, compound

Product 1

HCID 86588219HCID 86588219, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 164649Silver benzoateCatalystHCID 8471TriethylamineSolvent

Procedure

A mixture of 2.17 g (9.37 mmol) 1-(2-chloro-quinolin-5-yl)-2-diazo-ethanone and 20 mL methanol was brought to reflux. A solution of 0.20 g (0.87 mmol) silver benzoate in 1 mL triethylamine was added to the reaction mixture. After 10 min at reflux, TLC analysis (ethyl acetate, silica, Rf prod 0.8) showed starting material consumed. The solvent was removed under reduced pressure and the resulting black residue was purified on 100 g 230-400 mesh silica eluting with 1:1 hexanes/ethyl acetate to give 1.20 g (5.09 mmol, 55%) of (2-chloro-quinolin-5-yl)-acetic acid methyl ester as a white amorphous solid. MS (APCI) m/z 236 (M, 100% abundance), 238 (M+2, 32% abundance). 1H NMR (400 MHz) CDCl3 8.31 (d, J=8.9 Hz, 1H), 7.98 (d, J=8.5 Hz, 1H), 7.74 (m, 1H), 7.49 (d, J=7.2 Hz, 1H), 7.44 (d, J=8.9 Hz, 1H), 4.05 (s, 2H), 3.68 (s, 3H).

Workup

  1. temperatureto reflux
  2. temperatureAfter 10 min at reflux
  3. customconsumed
  4. customThe solvent was removed under reduced pressure
  5. customthe resulting black residue was purified on 100 g 230-400 mesh silica eluting with 1:1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-b6b9c2f6f9dc43aa84eb89d61bd2a76a
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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