Acetic Acid → HCID 12595986, compound

HRID 1701288Notes

Reaction equation

HRID 1701288 reaction equation
CN1CC[N:5]([C:8]2[C:14]3=[CH:15][CH:16]=[CH:17][N:13]3[CH2:12][C:11]3[CH:18]=[CH:19][CH:20]=[CH:21][C:10]=3[N:9]=2)CC1.C(O)(=O)C>[Zn].C(O)C>[NH2:5][C:8]1[C:14]2=[CH:15][CH:16]=[CH:17][N:13]2[CH2:12][C:11]2[CH:18]=[CH:19][CH:20]=[CH:21][C:10]=2[N:9]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 12617933HCID 12617933, compound

Product 1

HCID 12595986HCID 12595986, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 20 g. of 1-(o-nitrobenzyl)-2-pyrrolecarbonitrile [M. Artico et al.; See Example 1], 50 g. of zinc dust, 40 ml. of glacial acetic acid and 200 ml. of ethanol is stirred at room temperature for about 24 hr. The reaction mixture is filtered to remove unreacted zinc dust and the precipitate is washed with alcohol. The filtrate is chilled to 0° C. and the precipitated zinc salts are removed by filtration; this filtrate is then evaporated to a solid residue which is dissolved in methylene chloride and filtered again. The solvent is removed by evaporation and the residue crystallized by the addition of ether; the product is collected and 11-amino-5H-pyrrolo[2,1-c]-[1,4]benzodiazepine, m.p. 179°-181° C., is thereby obtained.

Workup

  1. additionA mixture of 20 g
  2. filtrationThe reaction mixture is filtered
  3. customto remove unreacted zinc dust
  4. washthe precipitate is washed with alcohol
  5. customthe precipitated zinc salts are removed by filtration
  6. customthis filtrate is then evaporated to a solid residue which
  7. dissolutionis dissolved in methylene chloride
  8. filtrationfiltered again
  9. customThe solvent is removed by evaporation
  10. customthe residue crystallized by the addition of ether
  11. customthe product is collected

Sources & evidence

ORD record
ord-224b8ea2e30f46b3b9c90ebc4af01268
Source dataset
uspto-grants-1980_03
Patent number
US04192803

Reaction notes

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