Sulfuric Acid → Benzanthrone

HRID 2082927Notes

Reaction equation

HRID 2082927 reaction equation
N[C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:11]([C:12](=[O:19])[C:13]4[C:18]=2[C:17]=1[CH:16]=[CH:15][CH:14]=4)=[CH:10][CH:9]=[CH:8][CH:7]=3.S(=O)(=O)(O)O.N([O-])=O.[Na+]>O>[CH:4]1[C:5]2=[C:18]3[C:13]([C:12]([C:11]4[C:6]2=[CH:7][CH:8]=[CH:9][CH:10]=4)=[O:19])=[CH:14][CH:15]=[CH:16][C:17]3=[CH:2][CH:3]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 131432163-AminobenzanthroneHCID 23668193Sodium Nitrite

Product 1

HCID 6697Benzanthrone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A 2 g amount of 3-aminobenzanthrone was dissolved in a mixture of 60 g of ice, 60 g of water and 15 ml of conc-sulfuric acid to obtain a solution. A solution of 2g of NaNO2 in 10 ml of water was gradually added to the solution. The mixture was stirred to react the components in order to obtain a diazonium salt of benzanthrone. The diazonium salt was gradually added to a solution of 5 g of KI in 10 ml of water and a small amount of copper powder was added to the solution. The mixture was heated to 80° C and reacted at 80° C for 1 hour and further at about 110° C for 1 hour. The resulting solid was extracted with hot benzene and treated with activated carbon and recrystallized from benzene whereby 3-iodobenzanthrone was obtained.

Workup

  1. customto obtain a solution
  2. customto react the components in order

Sources & evidence

ORD record
ord-c2e73121fb614cdcb1b5ec3a9cb186e4
Source dataset
uspto-grants-1978_04
Patent number
US04083725

Reaction notes

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