Acetone → 7-(2-Dimethylaminoethyl)amino-9-acetyl-6,9-dihydroxy-5,7,8,9,10,12-hexahydronaphthacene-5,12-dione

HRID 64906Notes

Reaction equation

HRID 64906 reaction equation
[CH3:1][N:2]([CH3:34])[CH2:3][CH2:4][NH:5][CH:6]1[CH2:23][CH:22]([OH:24])[CH2:21][C:20]2[CH:19]=[C:18]3[C:9]([C:10](=[O:32])[C:11]4[CH:12]=[CH:13][CH:14](CC)[C:15]5(OCCO5)[C:16]=4[C:17]3=[O:25])=[C:8]([OH:33])[C:7]1=2.Cl.[CH3:36][C:37](C)=[O:38]>>[CH3:34][N:2]([CH3:1])[CH2:3][CH2:4][NH:5][CH:6]1[CH2:23][C:22]([C:37](=[O:38])[CH3:36])([OH:24])[CH2:21][C:20]2[CH:19]=[C:18]3[C:9]([C:10](=[O:32])[C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=4[C:17]3=[O:25])=[C:8]([OH:33])[C:7]1=2

Participants

4

Reactant 3

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 86740997HCID 86740997, compound

Product 1

HCID 137124157-(2-Dimethylaminoethyl)amino-9-acetyl-6,9-dihydroxy-5,7,8,9,10,12-hexahydronaphthacene-5,12-dione

Procedure

7-(2-Dimethylaminoethyl)amino-9-(1,1-ethylenedioxy)ethyl-6,9-dihydroxy-5,7,8,9,10,12-hexahydronaphthacene-5,12-dione (60 mg) prepared in Example 13 (2) was added to a mixture of acetone (60 ml) and conc. hydrochloric acid (24 ml), and the resultant mixture was heated under reflux for 1 hour. After removal of acetone by distillation under reduced pressure, the water layer was washed with dichloromethane, adjusted to pH 8.0 with aqueous sodium hydroxide solution and extracted with dichloromethane. The extract was purified by silica gel chromatography using a mixture of chloroform and methanol (9:1) to give 7-(2-dimethylaminoethyl)amino-9-acetyl-6,9-dihydroxy-5,7,8,9,10,12-hexahydronaphthacene-5,12-dione (55 mg). M.P., 170°-172° C.

Workup

  1. temperatureunder reflux for 1 hour
  2. customAfter removal of acetone
  3. distillationby distillation under reduced pressure
  4. washthe water layer was washed with dichloromethane
  5. extractionextracted with dichloromethane
  6. customThe extract was purified by silica gel chromatography
  7. additiona mixture of chloroform and methanol (9:1)

Sources & evidence

ORD record
ord-4d630df49456478d92e62e4f843c1323
Source dataset
uspto-grants-1986_09
Patent number
US04610986

Reaction notes

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