Iodoethane → HCID 21931660, compound

HRID 1244021Notes

Reaction equation

HRID 1244021 reaction equation
CC(C)([O-])C.[K+].[CH2:7]1[CH2:11][O:10][CH2:9][CH2:8]1.OC1C=[C:15]2[C:20](=[CH:21][CH:22]=1)[N:19]([CH3:23])[C:18](=[O:24])[CH2:17][CH2:16]2.C(I)C>>[CH2:11]([O:10][C:9]1[CH:8]=[C:15]2[C:20](=[CH:21][CH:22]=1)[N:19]([CH3:23])[C:18](=[O:24])[CH2:17][CH2:16]2)[CH3:7]

Participants

4

Reactant 3

HCID 6340IodoethaneHCID 219318286-Hydroxy-1-methyl-3,4-dihydroquinolin-2(1H)-oneHCID 66863523KOtBu THF

Product 1

HCID 21931660HCID 21931660, compoundYield 33%

Procedure

1.0M potassium t-butoxide/THF (5.65 ml, 5.65 mmol) was added to 6-Hydroxy-1-methyl-3,4-dihydro-1H-quinolin-2-one (200 mg, 1.13 mmol) followed by the addition of ethyl iodide (452 μl, 5.65 mmol). The reaction mixture was stirred at room temperature for 2 hours and heated to 45° C. for an overnight. The salts were filtered off, rinsed with ethyl acetate and the combined filtrate was concentrated down to a residue. This was chromatographed using 1:1 ethylacetate/hexane to yield the title compound as a white solid (76 mg, 33% yield). 1H NMR (400 MHz, CDCl3) δ 1.36 (3H, t, J=6.9 Hz), 2.58 (2H, m), 2.82 (2H, m), 3.29 (3H, s), 3.96 (2H, q, J=7.0 Hz), 6.71 (2H, m), 6.84 (1H, d, J=8.7 Hz). m/z (APCI+) 206 (M+1). HPLC (aqueous 200 Mm ammonium acetate buffer/acetonitrile gradient, 3.0 ml/min, Hewlett Packard ODS Hypersil 5 μM, 125×4 mm column), 4.453 min.

Workup

  1. temperatureheated to 45° C. for an overnight
  2. filtrationThe salts were filtered off
  3. washrinsed with ethyl acetate
  4. concentrationthe combined filtrate was concentrated down to a residue
  5. customThis was chromatographed

Sources & evidence

ORD record
ord-f54709f9c95c4d82b06078dcb8b3b6d6
Source dataset
uspto-grants-2006_10
Patent number
US07119207B2

Reaction notes

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