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]=12Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
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
- filtrationfiltered
- additionTo the filtrate is added 0.5 g of 10% Pd/C
- additionAn additional 0.5 g of 10% Pd/C is added
- waithydrogenation continued for 25 hours at 65 psi
- filtrationThe mixture is filtered through diatomaceous earth
- washthe cake washed with ethyl acetate
- customThe filtrate is evaporated in vacuo to a residue which
- dissolutionis dissolved in methylene chloride
- additiontreated with activated carbon
- filtrationfiltered through diatomaceous earth and hexanes
- additionadded to the filtrate at the boil
Sources & evidence
- ORD record
- ord-770cf2f27fad497c8b1a5a3862792260
- Source dataset
- uspto-grants-1997_03
- Patent number
- US05612334
Linked notes
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