Nitric Acid → HCID 14209946, compound

HRID 1492167Notes

Reaction equation

HRID 1492167 reaction equation
[CH3:1][C:2]1([CH3:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4](=[O:12])[CH2:3]1.S(=O)(=O)(O)O.[N+:19]([O-])([OH:21])=[O:20]>>[CH3:1][C:2]1([CH3:13])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:19]([O-:21])=[O:20])[CH:10]=2)[NH:5][C:4](=[O:12])[CH2:3]1

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric Acid2×HCID 142099454,4-Dimethyl-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 14209946HCID 14209946, compound

Procedure

To 17.5 g. (0.1 mole) 1,2,3,4-tetrahydro-4,4-dimethylquinolin-2-one in 200 ml. 80% sulphuric acid is added dropwise, while cooling with ice, a mixture of 5 ml. 96% nitric acid and 20 ml. 80% sulphuric acid, followed by stirring for 1 hour at ambient temperature. Subsequently, the reaction mixture is poured on to ice and the crystallisate is filtered off with suction and then washed with water. The crude product is purified by column chromatography on silica gel with butan-2-one/ethyl acetate (20/1 v/v) as elution agent. Yield 17.2 g. (78% of theory); m.p. 202°-204° C.

Workup

  1. temperaturewhile cooling with ice
  2. additiona mixture of 5 ml
  3. additionSubsequently, the reaction mixture is poured on to ice
  4. filtrationthe crystallisate is filtered off with suction
  5. washwashed with water
  6. customThe crude product is purified by column chromatography on silica gel with butan-2-one/ethyl acetate (20/1 v/v) as elution agent

Sources & evidence

ORD record
ord-4331733c10844c578216a985b27b5fbb
Source dataset
uspto-grants-1994_12
Patent number
US05373019

Reaction notes

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