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

HRID 55166

반응식

HRID 55166 반응식
[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

참가 물질

3

반응물 1

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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. filtrationThe mixture is filtered through diatomaceous earth
  5. washthe cake washed with ethyl acetate
  6. customThe filtrate is evaporated in vacuo to a residue which
  7. dissolutionis dissolved in methylene chloride
  8. additiontreated with activated carbon
  9. filtrationfiltered through diatomaceous earth and hexanes
  10. additionadded to the filtrate at the boil

출처 및 근거

ORD 기록
ord-d66fda10315c49e1872f85a5689cd579
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05624923

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