HCID 69654722, compound → HCID 21069366, compound

HRID 1244016Notes

Reaction equation

HRID 1244016 reaction equation
[CH2:1]([Li])CCC.[CH3:6][O:7][C:8](=[O:25])[C:9]([C:11]1[CH:20]=[C:19]2[C:14]([CH2:15][CH2:16][C:17](=[O:22])[N:18]2[CH3:21])=[CH:13][C:12]=1[O:23][CH3:24])=O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[CH3:6][O:7][C:8](=[O:25])[C:9]([C:11]1[CH:20]=[C:19]2[C:14]([CH2:15][CH2:16][C:17](=[O:22])[N:18]2[CH3:21])=[CH:13][C:12]=1[O:23][CH3:24])=[CH2:1]

Participants

5

Reactant 2

HCID 69654722HCID 69654722, compoundHCID 178418339Butyllithium

Product 1

HCID 21069366HCID 21069366, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-20 °C

Procedure

A suspension of 3.1 g (0.0087 m) of methyl-triphenylphosphonium bromide in 100 ml of tetrahydrofuran was cooled to −20° C. To this suspension was added dropwise 3.5 ml (0.0087 m) of a 2.5 M solution of n-butyl lithium in tetrahydrofuran. The mixture was slowly. warmed to +5° C. at which time a yellow solution formed. The mixture was cooled to −20° C. and 2.2 g (0.0079 m) of (6-methoxy-1-methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-7-yl)-oxo-acetic acid methyl ester was added. The reaction mixture was warmed to room temperature and stirred for 18 hours. The reaction mixture was filtered, and the filtrate evaporated to yield a brown oily residue. This material was chromatographed on 75 grams of silica using chloroform as the elutant. Appropriate fractions were combined and evaporated to yield 1.8 g (83%) of 2-(6-methoxy-1-methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-7-yl) acrylic acid methyl ester as an amorphous solid. 1H NMR (CDCl3) δ 2.58 (m, 2H), 2.82 (m, 2H), 3.15 (s, 3H), 3.70 (s, 6H), 5.70 (s, 1H), 6.25 (s, 1H), 6.65 (s, 1H), 6.80 (s, 1H). Mass spectrum: m/e=276 (p+1). TLC (5/1 methylene chloride/ethyl acetate) Rf=0.90.

Workup

  1. temperaturewarmed to +5° C. at which time a yellow solution
  2. customformed
  3. temperatureThe mixture was cooled to −20° C.
  4. temperatureThe reaction mixture was warmed to room temperature
  5. filtrationThe reaction mixture was filtered
  6. customthe filtrate evaporated
  7. customto yield a brown oily residue
  8. customThis material was chromatographed on 75 grams of silica
  9. customevaporated

Sources & evidence

ORD record
ord-2e3e38aaf5e5471c8bafd9e86f3b88de
Source dataset
uspto-grants-2006_10
Patent number
US07119207B2

Reaction notes

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