N-Methylcyclohexylamine → 4-(Cyclohexylmethylamino)-1,2-naphthoquinone

HRID 1639016Notes

Reaction equation

HRID 1639016 reaction equation
[CH:1]1[CH:6]=[C:5]2[C:7](S([O-])(=O)=O)=[CH:8][C:9]([C:11](=[O:12])[C:4]2=[CH:3][CH:2]=1)=[O:10].[Na+].[CH3:18][NH:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1>O>[CH3:18][N:19]([CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)[C:7]1[C:5]2[C:4](=[CH:3][CH:2]=[CH:1][CH:6]=2)[C:11](=[O:12])[C:9](=[O:10])[CH:8]=1

Participants

4

Reactant 2

HCID 7514N-MethylcyclohexylamineHCID 516996Sodium beta-naphthoquinone-4-sulfonate

Product 1

HCID 30822374-(Cyclohexylmethylamino)-1,2-naphthoquinone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 10.4 g of 1,2-naphthoquinone-4-sulfonic acid-sodium salt in 350 ml of water is stirred at room temperature for 30 minutes. To this solution is added 4.52 g of N-methylcyclohexylamine in one portion. The solution is stirred five hours at room temperature and the precipitate then filtered. The product is washed with 200 ml of water and dried at 100° C. in vacuo overnight to afford 4-(N-methylcyclohexylamino)-1,2-naphthoquinone melting at 168°-170° C. The preparation of the same compound from 4-ethoxy-1,2-naphthoquinone is reported in J. Med. Chem. 13, 97 (1970).

Workup

  1. filtrationthe precipitate then filtered
  2. washThe product is washed with 200 ml of water
  3. customdried at 100° C. in vacuo overnight

Sources & evidence

ORD record
ord-b97021d36b5742d7a1edea97c11be0eb
Source dataset
uspto-grants-1989_11
Patent number
US04882339

Reaction notes

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