Sodium Hydroxide → 1-Aminoanthraquinone

HRID 1731009Notes

Reaction equation

HRID 1731009 reaction equation
[OH-].[Na+].[N+:3]([C:6]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:7]=1[C:8](=[O:21])[C:9]1[CH2:10][CH2:11][CH2:12][CH2:13][C:14]=1[C:15]2=[O:20])([O-])=O.[H][H]>[Pd].COCCO>[NH2:3][C:6]1[C:7]2[C:8](=[O:21])[C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:15](=[O:20])[C:16]=2[CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 21292556HCID 21292556, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 67101-AminoanthraquinoneYield 110.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 80192-MethoxyethanolSolvent

Procedure

0.026 Gram of a 5% palladium on carbon catalyst and 3.0 grams of a 20% aqueous sodium hydroxide solution were added to a mixture of 2.6 grams of 5-nitrotetrahydroanthraquinone and 101 grams of methyl cellosolve, into which was fed hydrogen for having hydrogen absorbed at room temperature under normal pressure in the 5-nitro compound in an amount of 1.1 mols per mol of the 5-nitro compound. A small amount of reddish brown crystals were precipitated. The reaction solution was subjected to filtration, followed by washing with methyl cellosolve. The filtrate and washings were combined together and neutralized with dilute sulfuric acid. Then, the resultant solution was concentrated under reduced pressure to obtain crystals which were separated by filtration, washed with methanol and then with water, and dried to obtain 2.5 grams of 1-aminoanthraquinone. The purity was 97.8% and the yield was 93.3%.

Workup

  1. customabsorbed at room temperature under normal pressure in the 5-nitro compound in an amount of 1.1 mols per mol of the 5-nitro compound
  2. customA small amount of reddish brown crystals were precipitated
  3. filtrationThe reaction solution was subjected to filtration
  4. washby washing with methyl cellosolve
  5. concentrationThen, the resultant solution was concentrated under reduced pressure
  6. customto obtain crystals which
  7. customwere separated by filtration
  8. washwashed with methanol
  9. dry with materialwith water, and dried

Sources & evidence

ORD record
ord-c95813e0c98b4893b3daa37bca8a7f5c
Source dataset
uspto-grants-1976_11
Patent number
US03994932

Reaction notes

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