Acetic Acid → HCID 21449232, compound

HRID 596934Notes

Reaction equation

HRID 596934 reaction equation
[CH3:1][O:2][C:3]1[C:20]2[C:19](=[O:21])[C:18]3[C:9](=[C:10]([OH:24])[C:11]4[CH2:12][C:13](=[O:23])[CH2:14][CH2:15][C:16]=4[C:17]=3[OH:22])[C:8](=[O:25])[C:7]=2[CH:6]=[CH:5][CH:4]=1.[C-:26]#[N:27].[K+].CC(O)=O>C(Cl)(Cl)Cl.CCO.O>[CH3:1][O:2][C:3]1[C:20]2[C:19](=[O:21])[C:18]3[C:9](=[C:10]([OH:24])[C:11]4[CH2:12][C:13]([C:26]#[N:27])([OH:23])[CH2:14][CH2:15][C:16]=4[C:17]=3[OH:22])[C:8](=[O:25])[C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 9032Potassium CyanideHCID 133178885,12-Dihydroxy-7-methoxy-3,4-dihydrotetracene-2,6,11(1H)-trione

Product 1

HCID 21449232HCID 21449232, compoundYield 77.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21889567Chloroform ethanolSolvent

Procedure

4-Methoxy-6,11-dihydroxy-7,8-dihydro-5,9 (10H),12-naphthacenetrione (IV) (45.3 mg, 0.134 mmole) and KCN (300 mg) were placed in 50% CHCl3 /EtOH (8 ml) and cooled to 0°. HOAc (0.4 ml) was added and the mixture was stirred at 23° for 5 hr. The reaction mixture was diluted with H2O (15 ml), the organic phase separated and the aqueous phase extracted with CHCl3 (10 ml). The organic solutions were combined, dried over Na2SO4 and evaporated. The residue was chromatographed (8 g silica gel, 98.2 CHCl3 /MeOH) to afford 38.0 mg (77%) of (V): mp 232°-235° (dec); irnujol 2.93 (OH), 6.20, 6.31 μ (chelated quinone); pmr 100 MHz CDCl3 δ 2.1-2.4 (m, 2H, 8-H2), 2.8-3.4 (m, 5H, benzylic H's and 9-OH), 4.08 (s, 3H, OMe), 7.36 (dd, 1H, J = 8Hz and J = 1Hz, 3-H), 7.74 (t, 1H, J = 8Hz, 2-H), 7.99 (dd, 1H, J = 8Hz and J = 1Hz, 1-H), 13.28 (s, 1H, phenolic OH), 13.68 (s, 1H, phenolic OH); ms 12 ev m/e (%) 338 M-HCN (100).

Workup

  1. temperaturecooled to 0°
  2. customthe organic phase separated
  3. extractionthe aqueous phase extracted with CHCl3 (10 ml)
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe residue was chromatographed (8 g silica gel, 98.2 CHCl3 /MeOH)

Sources & evidence

ORD record
ord-b90ec420f4f749609d81e2121a4fabe1
Source dataset
uspto-grants-1977_03
Patent number
US04012448

Reaction notes

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