Formaldehyde → 1-Aminoanthraquinone

HRID 464926Notes

Reaction equation

HRID 464926 reaction equation
[N+:1]([C:4]1[C:17]2[C:16](=[O:18])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9](=[O:19])[C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-])=O.ClC1C(=O)C2C(C(=O)C=1Cl)=CC=CC=2.[OH-].[Na+].C=O>C(O)C>[NH2:1][C:4]1[C:17]2[C:16](=[O:18])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9](=[O:19])[C:8]=2[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 67041-NitroanthraquinoneHCID 8342DichloneHCID 14798Sodium Hydroxide

Product 1

HCID 67101-Aminoanthraquinone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

76 parts of 1-nitroanthraquinone and 0.6 part of 2,3-dichloro-1,4-naphthoquinone in 300 parts by volume of ethanol and 150 parts by volume of 50% aqueous sodium hydroxide solution are heated to 78°-80° C. At this temperature, 37% aqueous formaldehyde solution is added dropwise to the solution in accordance with the consumption. The consumption of formaldehyde can be checked and the addition controlled by measuring the changes in the redox potential. The time taken for the addition is 11/2 to 2 hours. The 1-aminoanthraquinone so obtained is then completely precipitated by addition of water, and the precipitate is isolated by filtration, washed with water and dried in vacuo at 80° C. Yield: about 61 g (~91% of theory) of 1-aminoanthraquinone.

Workup

  1. customThe consumption of formaldehyde
  2. additionthe addition
  3. additionThe time taken for the addition
  4. custom2 to 2 hours

Sources & evidence

ORD record
ord-fa49445f3f3b4c89a0e6b0c152e9bfa6
Source dataset
uspto-grants-1985_10
Patent number
US04549989

Reaction notes

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