Carbonate Ion → 4,4,8-Trimethyl-3,4-dihydroquinolin-2(1H)-one

HRID 1198947Notes

Reaction equation

HRID 1198947 reaction equation
[O:1]=[C:2]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH3:14])[CH:3]=[C:4]([CH3:6])[CH3:5].C(=O)([O-])[O-]>S(=O)(=O)(O)O>[CH3:5][C:4]1([CH3:6])[C:13]2[C:8](=[C:9]([CH3:14])[CH:10]=[CH:11][CH:12]=2)[NH:7][C:2](=[O:1])[CH2:3]1

Participants

4

Reactant 2

HCID 19660Carbonate IonHCID 191774333-Methyl-N-(2-methylphenyl)but-2-enamide

Product 1

HCID 198677004,4,8-Trimethyl-3,4-dihydroquinolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

N-(1-oxo-3-methyl-but-2-en-yl)-2-methylaniline (0.5 g) was added with stirring to 98% w/w sulphuric acid (10 cm3) at 0°. After 2 hours at room temperature (20°) the mixture was poured carefully onto ice (30 g) and the resulting solution was basified to pH 9 with saturated carbonate solution. The mixture was then extracted wilth dichloromethane (2×200 cm3), and the combined and dried (MgSO4) organic extracts were evaporated in vacuo to give a solid which was chromatographed on silica (Merck "MK 60.9385" [Trade mark]). Elution with dichloromethane, followed by combination and evaporation of appropriate fractions gave the title compound, m.p. 120° (0.21 g).

Workup

  1. additionAfter 2 hours at room temperature (20°) the mixture was poured carefully onto ice (30 g)
  2. extractionThe mixture was then extracted wilth dichloromethane (2×200 cm3)
  3. dry with materialdried (MgSO4) organic extracts
  4. customwere evaporated in vacuo
  5. customto give a solid which
  6. customwas chromatographed on silica (Merck "MK 60.9385" [Trade mark])
  7. washElution with dichloromethane
  8. customfollowed by combination and evaporation of appropriate fractions

Sources & evidence

ORD record
ord-e8e117d40bb54295a129c44fc9c5f290
Source dataset
uspto-grants-1990_02
Patent number
US04898872

Reaction notes

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