1-(o-Nitrobenzyl)-imidazole-2-carboxaldehyde → 5H-Imidazo(2,1-c)(1,4)benzodiazepine, 10,11-dihydro-

HRID 3519Notes

Reaction equation

HRID 3519 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][CH:15]=[CH:14][C:5]=1[CH2:6][N:7]1[CH:11]=[CH:10][N:9]=[C:8]1[CH:12]=O)([O-])=O>C(O)C>[N:9]1[CH:10]=[CH:11][N:7]2[CH2:6][C:5]3[CH:14]=[CH:15][CH:16]=[CH:17][C:4]=3[NH:1][CH2:12][C:8]=12

Participants

3

Reactant 1

HCID 127249851-(o-Nitrobenzyl)-imidazole-2-carboxaldehyde

Product 1

HCID 30603995H-Imidazo(2,1-c)(1,4)benzodiazepine, 10,11-dihydro-

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 5.0 g sample of 1-(o-nitrobenzyl)-imidazole-2-carboxaldehyde is dissolved in 150 ml of hot ethyl alcohol, cooled to room temperature and filtered. To the filtrate is added 0.5 g of 10% Pd/C and the mixture hydrogenated at 48 psi for 4 hours. An additional 0.5 g of 10% Pd/C is added and hydrogenation continued for 25 hours at 65 psi. The mixture is filtered through diatomaceous earth and the cake washed with ethyl acetate. The filtrate is evaporated in vacuo to a residue which is dissolved in methylene chloride, treated with activated carbon, filtered through diatomaceous earth and hexanes added to the filtrate at the boil to give 1.86 g of the desired product as a crystalline solid, m.p. 164°-170° C.

Workup

  1. filtrationfiltered
  2. additionTo the filtrate is added 0.5 g of 10% Pd/C
  3. additionAn additional 0.5 g of 10% Pd/C is added
  4. waithydrogenation continued for 25 hours at 65 psi
  5. filtrationThe mixture is filtered through diatomaceous earth
  6. washthe cake washed with ethyl acetate
  7. customThe filtrate is evaporated in vacuo to a residue which
  8. dissolutionis dissolved in methylene chloride
  9. additiontreated with activated carbon
  10. filtrationfiltered through diatomaceous earth and hexanes
  11. additionadded to the filtrate at the boil

Sources & evidence

ORD record
ord-3b609f87b5c246a3b15b45db6d0f89d5
Source dataset
uspto-grants-1998_03
Patent number
US05733905

Reaction notes

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