Hydrochloric Acid → 2,3-Dimethoxy-naphthacene-5,12-dione

HRID 275080

Reaction equation

HRID 275080 reaction equation
F[C:2]1[C:19](F)=[CH:18][C:17]2[C:16](=[O:21])[C:15]3[C:6](=[CH:7][C:8]4[C:13]([CH:14]=3)=[CH:12][CH:11]=[CH:10][CH:9]=4)[C:5](=[O:22])[C:4]=2[CH:3]=1.[C:23]([O-:26])([O-])=O.[K+].[K+].[CH3:29][OH:30].Cl>CS(C)=O>[CH3:29][O:30][C:2]1[C:19]([O:26][CH3:23])=[CH:18][C:17]2[C:16](=[O:21])[C:15]3[C:6](=[CH:7][C:8]4[C:13]([CH:14]=3)=[CH:12][CH:11]=[CH:10][CH:9]=4)[C:5](=[O:22])[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 11430Potassium CarbonateHCID 200898342,3-Difluoronaphthacene-5,12-dione

Product 1

HCID 111745752,3-Dimethoxy-naphthacene-5,12-dione

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1 g (3.4 mmol) of 2,3-difluoro-naphthacene-5,12-dione, 0.94 g (6.8 mmol) of K2CO3, 2.18 g of methanol and 20 ml of DMSO are stirred at 110° C. for 22 hours. The mixture is poured onto dilute hydrochloric acid. The product is filtered off, washed four times with water, dried and recrystallized from CH2Cl2 /pentane; yield 0.72 g (67%); melting point >250° C.

Workup

  1. filtrationThe product is filtered off
  2. washwashed four times with water
  3. customdried
  4. customrecrystallized from CH2Cl2 /pentane

Sources & evidence

ORD record
ord-e5097bd68377463983c1e1c315f75eae
Source dataset
uspto-grants-1995_02
Patent number
US05391749

Linked notes

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