Cyclohexanol → 1-Aminoanthraquinone

HRID 1731008Notes

Reaction equation

HRID 1731008 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.C1(O)CCCCC1.[H][H]>[Ni]>[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 4

HCID 7966CyclohexanolHCID 14798Sodium HydroxideHCID 21292556HCID 21292556, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 67101-AminoanthraquinoneYield 82.8%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Conditions

Temperature
100 °C

Procedure

3 Grams of a Raney nickel catalyst and 100 grams of a 20% aqueous sodium hydroxide solution were added to a mixture of 128 grams of 5-nitrotetrahydroanthraquinone and 1,700 grams of cyclohexanol, into which was fed hydrogen while agitating at 100° C. for having hydrogen absorbed in the starting 5-nitro compound in an amount of 2 mols per mol of the 5-nitro compound. After completion of hydrogenation, the catalyst was separated by filtration and air was passed into the resultant filtrate at 30° C. for 1 hour. The resultant solution was cooled to 10° C. to precipitate crystals, which were then separated by filtration, washed with water and dried to obtain 92 grams of 1-aminoanthraquinone having a purity of 98.2%.

Workup

  1. customabsorbed in the starting 5-nitro compound in an amount of 2 mols per mol of the 5-nitro compound
  2. customAfter completion of hydrogenation, the catalyst was separated by filtration and air
  3. temperatureThe resultant solution was cooled to 10° C.
  4. customto precipitate crystals, which
  5. customwere then separated by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-72e00d43b01645bdb8b0c3e08c2b688d
Source dataset
uspto-grants-1976_11
Patent number
US03994932

Reaction notes

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