Nitric Acid → HCID 19867711, compound

HRID 1198946Notes

Reaction equation

HRID 1198946 reaction equation
S(=O)(=O)(O)O.[CH3:6][C:7]1([CH3:19])[C:16]2[C:11](=[C:12]([CH3:17])[CH:13]=[CH:14][CH:15]=2)[NH:10][C:9](=[O:18])[CH2:8]1.C(=O)([O-])[O-].[Na+].[Na+].[N+:26]([O-])([OH:28])=[O:27]>>[CH3:6][C:7]1([CH3:19])[C:16]2[C:11](=[C:12]([CH3:17])[CH:13]=[C:14]([N+:26]([O-:28])=[O:27])[CH:15]=2)[NH:10][C:9](=[O:18])[CH2:8]1

Participants

5

Reactant 4

HCID 944Nitric AcidHCID 1118Sulfuric Acid2×HCID 10340Sodium CarbonateHCID 198677004,4,8-Trimethyl-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 19867711HCID 19867711, compound

Procedure

A mixture of concentrated nitric acid (10 cm3, S.G.=1.42) and 98% w/w sulphuric acid (25 cm3) was added dropwise to a stirred solution of 3,4-dihydro-4,4,8-trimethyl-2-(1H)-quinolone (6 g) in 98% w/w sulphuric acid (25 cm3) cooled to -10°. The temperature was maintained at -10° for a further 30 minutes, the mixture poured onto ice (200 g), basified to pH 9 with saturated sodium carbonate solution and extracted with methanol:chloroform, 1:20 by volume (2×300 cm3). The combined and dried (MgSO4) organic extracts were evaporated in vacuo to give the title compound (6.46 g) which was characterised spectroscopically and used directly in Preparation 24 without further purification.

Workup

  1. temperaturecooled to -10°
  2. temperatureThe temperature was maintained at -10° for a further 30 minutes
  3. additionthe mixture poured onto ice (200 g)
  4. extractionextracted with methanol
  5. dry with materialdried (MgSO4) organic extracts
  6. customwere evaporated in vacuo

Sources & evidence

ORD record
ord-651a0f33bbf8402c83cdbdee82bca7ef
Source dataset
uspto-grants-1990_02
Patent number
US04898872

Reaction notes

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