Sulfuric Acid → HCID 178421831, compound

HRID 328604Notes

Reaction equation

HRID 328604 reaction equation
N([C:8]1[C:9](=[O:21])[C:10]2[C:15]([C:16](=[O:18])[CH:17]=1)=[CH:14][C:13]([CH3:19])=[C:12]([CH3:20])[CH:11]=2)C1C=CC=CC=1.S(=O)(=O)(O)[OH:23]>O>[CH3:19][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][C:12]=1[CH3:20])[C:9](=[O:21])[C:8]([OH:23])=[CH:17][C:16]2=[O:18]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 12369068HCID 12369068, compound

Product 1

HCID 178421831HCID 178421831, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 2-anilino-6,7-dimethyl-1,4naphthoquinone (3.1; 0.014 mole) in concentrated sulphuric acid (70ml) was diluted with an equal volume of water and refluxed for 1 minute. After pouring into cold water the precipitated hydroxy derivative was filtered off and extracted into petrol ether (b.p. 100°-102° C). After treatment of the extract with charcoal the title compound separated as a yellow solid, 1.29g (55%), m.p. 175°-177° C (d). (Found; C, 71.29; H, 5.07 C12H10O3 requires; C, 71.28; H, 4.98%)

Workup

  1. temperaturerefluxed for 1 minute
  2. filtrationwas filtered off
  3. extractionextracted into petrol ether (b.p. 100°-102° C)
  4. extractionAfter treatment of the extract with charcoal the title compound
  5. customseparated as a yellow solid, 1.29g (55%), m.p. 175°-177° C (d)

Sources & evidence

ORD record
ord-8c8202d2fdb7460b9ca57a6b79d0745a
Source dataset
uspto-grants-1977_04
Patent number
US04017639

Reaction notes

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