Aniline → HCID 12369068, compound

HRID 328603Notes

Reaction equation

HRID 328603 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH3:12])[C:8](=[O:13])[CH:7]=[CH:6][C:5]2=[O:14].[NH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(O)C>[NH:15]([C:7]1[C:8](=[O:13])[C:9]2[C:4]([C:5](=[O:14])[CH:6]=1)=[CH:3][C:2]([CH3:1])=[C:11]([CH3:12])[CH:10]=2)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 2463546,7-dimethyl-1,4-naphthoquinone

Product 1

HCID 12369068HCID 12369068, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a warm solution of 6,7-dimethyl-1,4-naphthoquinone (1.08g; 0.058 mole) in ethanol (20ml) was added aniline (0.5ml) and the red solution refluxed for 1 hr. on a steam bath. After standing overnight the red crystalline anilino derivative was filtered off and recrystallised from acetic acid; water to give 0.54g (34%) of material of m.p. 208°-210° C. (Found C, 78.02; H, 5,47; N, 4.88; C18H15NO2 requires; C, 77.96; H, 5.45; N, 5.05%).

Workup

  1. temperaturethe red solution refluxed for 1 hr
  2. filtrationthe red crystalline anilino derivative was filtered off
  3. customrecrystallised from acetic acid

Sources & evidence

ORD record
ord-c3673994c9f548908b1be4b3bd458132
Source dataset
uspto-grants-1977_04
Patent number
US04017639

Reaction notes

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