4-(Cyclohexylmethylamino)-1,2-naphthoquinone → 1,2-Naphthalenediol, 4-(cyclohexylmethylamino)-, 1,2-diacetate

HRID 1639015Notes

Reaction equation

HRID 1639015 reaction equation
[CH3:1][N:2]([CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](=[O:13])[C:5](=[O:14])[CH:4]=1.[H][H]>C(OC(=O)C)(=O)C.[Pd]>[CH3:1][N:2]([CH:15]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1)[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13][C:6](=[O:13])[CH3:7])=[C:5]([O:14][C:5](=[O:14])[CH3:4])[CH:4]=1

Participants

5

Reactant 2

HCID 30822374-(Cyclohexylmethylamino)-1,2-naphthoquinoneHCID 178418361HCID 178418361, compound

Product 1

HCID 1294371,2-Naphthalenediol, 4-(cyclohexylmethylamino)-, 1,2-diacetate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 7918Acetic AnhydrideSolvent

Procedure

A suspension of 3.5 g of 4-(N-methylcyclohexylamino)-1,2-naphthoquinone in 50 ml of acetic anhydride is hydrogenated at 45 lbs pressure and room temperature using 1.2 g of 10% palladium on carbon as catalyst. After uptake of hydrogen ceases and the red color of the solution is discharged (5 hours) the catalyst is removed by filtration. The acetic anhydride is evaporated under reduced pressure at 60° C. and the residue is taken up in toluene, treated with charcoal and filtered. The toluene solution is evaporated under reduced pressure and the product crystallized from 1:1 hexane-diethyl ether (100 ml) to afford 4-(N-methylcyclohexylamino)-1,2-diacetoxynaphthalene, the compound of formula II wherein NR1R2 represents N-methylcyclohexylamino, R3 represents hydrogen, and R4 and R5 represent acetyl, m.p. 103°-105° C.; hydrochloride salt, m.p. 165°-167° C.

Workup

  1. customis hydrogenated at 45 lbs pressure and room temperature
  2. custom(5 hours)
  3. customis removed by filtration
  4. customThe acetic anhydride is evaporated under reduced pressure at 60° C.
  5. additiontreated with charcoal
  6. filtrationfiltered
  7. customThe toluene solution is evaporated under reduced pressure
  8. customthe product crystallized from 1:1 hexane-diethyl ether (100 ml)

Sources & evidence

ORD record
ord-4b360a84c5914eada831ee416d42b735
Source dataset
uspto-grants-1989_11
Patent number
US04882339

Reaction notes

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