Formaldehyde → 1-Amino-2-methylanthraquinone

HRID 464927

Reaction equation

HRID 464927 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][C:5]=1[CH3:20])([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][C:5]=1[CH3:20]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 8342DichloneHCID 14798Sodium HydroxideHCID 314262-Methyl-1-nitroanthraquinone

Product 1

HCID 67021-Amino-2-methylanthraquinone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

53 parts of 1-nitro-2-methylanthraquinone 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-amino-2-methylanthraquinone 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 43 g (~90% of theory) of 1-amino-2-methylanthraquinone.

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-2651892294d0474baa1b50f75fd8a23b
Source dataset
uspto-grants-1985_10
Patent number
US04549989

Linked notes

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