Nitric Acid → HCID 14209946, compound

HRID 703927Notes

Reaction equation

HRID 703927 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 pured 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. filtrationthe crystallisate is filtered off with suction
  4. washwashed with water
  5. 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-f0658c75f7f04b6b8de9ac0f16eb26c2
Source dataset
uspto-grants-1991_01
Patent number
US04985448

Reaction notes

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