Acetic Acid → HCID 12929158, compound

HRID 894182Notes

Reaction equation

HRID 894182 reaction equation
[CH2:1]1[O:21][C:20]2[C:3](=[CH:4][C:5]3[C:11](=[O:12])[C:10]4[CH:13]=C(C#N)[CH:15]=[CH:16][C:9]=4[CH2:8][O:7][C:6]=3[CH:19]=2)[O:2]1.Cl.[C:23]([OH:26])(=[O:25])[CH3:24]>>[CH2:1]1[O:21][C:20]2[C:3](=[CH:4][C:5]3[C:11](=[O:12])[C:10]4[CH:13]=[C:24]([C:23]([OH:26])=[O:25])[CH:15]=[CH:16][C:9]=4[CH2:8][O:7][C:6]=3[CH:19]=2)[O:2]1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 12929159HCID 12929159, compound

Product 1

HCID 12929158HCID 12929158, compound

Procedure

Heat a mixture of 4.98 gm. (0.0178 mole) of 6,11-dihydro-2,3-methylenedioxy-11-oxodibenz[b,e]-oxepin-9-carbonitrile, 90 ml. of acetic acid, 9 ml. of concentrated hydrochloric acid under reflux of 74 hours. Cool the reaction mixture and separate the solids by filtration and dry (yield 3.45 gm.). Suspend the solids in water and treat with N-methylpiperazine. Remove base insolubles by filtration and acidify the filtrate with concentrated hydrochloric acid to the Congo Red end point. Separate the solids by filtration and dry. Purify by recrystallization from acetic acid to obtain the title product (m.p. 320°-321° C.)

Workup

  1. temperatureHeat
  2. additiona mixture of 4.98 gm
  3. temperatureCool the reaction mixture
  4. customseparate the solids
  5. filtrationby filtration
  6. customdry (yield 3.45 gm.)
  7. additiontreat with N-methylpiperazine
  8. customRemove base insolubles
  9. filtrationby filtration
  10. customSeparate the solids
  11. filtrationby filtration
  12. customdry
  13. customPurify by recrystallization from acetic acid

Sources & evidence

ORD record
ord-6178c6736e674196a8c6d0e30e9c62bd
Source dataset
uspto-grants-1981_08
Patent number
US04282365

Reaction notes

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