2-[2-[(2-Nitrophenyl)methyl]3-thienyl]-1,3-dioxolane → 4,10-Dihydro-5H-thieno[3,2-c][1]benzazepine

HRID 355873Notes

Reaction equation

HRID 355873 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]1[S:12][CH:13]=[CH:14][C:15]=1[CH:16]1OCCO1)([O-])=O>CC(C)=O.C(O)(=O)C.[Zn]>[S:12]1[C:11]2[CH2:10][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[NH:1][CH2:16][C:15]=2[CH:14]=[CH:13]1

Participants

5

Reactant 1

HCID 111300652-[2-[(2-Nitrophenyl)methyl]3-thienyl]-1,3-dioxolane

Product 1

HCID 108673664,10-Dihydro-5H-thieno[3,2-c][1]benzazepineYield 72.4%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 180AcetoneSolvent

Procedure

A stirred solution of 4 gms of 2-[2-[(2-nitrophenyl)methyl]-3-thienyl]-1,3-dioxolane in acetone (50 ml) and acetic acid (90% 50 ml) is heated to 60° C. Zinc dust (10 gms) is slowly added and after the addition, reaction mixture is stirred for 6 hours. At the end, reaction mixture is filtered and the residue washed with acetone and concentrated. The brown residue is extracted with chloroform and washed well with water. The organic layer is dried (Na2SO4) and filtered and concentrated. The product is isolated by silica gel column chromatography by eluting with 20% ethyl acetate:hexane to give 2.0 g of the desired product as a pale yellow crystalline solid, m.p. 86° C. Mass Spectrum; M+ 202.

Workup

  1. additionafter the addition, reaction mixture
  2. customAt the end, reaction mixture
  3. filtrationis filtered
  4. washthe residue washed with acetone
  5. concentrationconcentrated
  6. extractionThe brown residue is extracted with chloroform
  7. washwashed well with water
  8. dry with materialThe organic layer is dried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe product is isolated by silica gel column chromatography
  12. washby eluting with 20% ethyl acetate

Sources & evidence

ORD record
ord-7efa85d0fd3644c6998fdf70402873b6
Source dataset
uspto-grants-1998_11
Patent number
US05834461

Reaction notes

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