4-Nitrobenzimidazole → 7-Aminobenzimidazole

HRID 1056894노트

반응식

HRID 1056894 반응식
[N+:1]([C:4]1[C:12]2[N:11]=[CH:10][NH:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-])=O>CC(O)=O.[Pd]>[NH:9]1[C:8]2[CH:7]=[CH:6][CH:5]=[C:4]([NH2:1])[C:12]=2[N:11]=[CH:10]1

참가 물질

4

반응물 1

HCID 1609494-Nitrobenzimidazole

생성물 1

HCID 203297-Aminobenzimidazole

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 176Acetic Acid용매

실험 절차

4-Nitro-1H-benzimidazole was hydrogenated (48 psi) with 1 g 10% Pd/C in HOAc (100 mL) for 3 h. The crude mixture was filtered through a pad of Celite, washing with MeOH, and concentrated. The residue was taken up in 2 M aq HCl and applied to a Phenomenex Strata-X-C ion exchange column (5 g). The column was washed with H20 and MeOH, The washings contained additional material and were applied to another Strata X-C ion exchange column (5 g). The columns were washed with H20 and MeOH. Each of the columns containing product were washed separately with 10% concentrated NH4OH in MeOH and the product collected in fractions. The collected fractions were concentrated to give 1H-Benzimidazol-4-amine as a deep red solid. 1H NMR (500 MHz, d6-DMSO) δ 12.10 (bs, 1H), 7.98 (s, 1H), 6.87 (t, J=7.81 Hz, 1H), 6.72 (d, J=7.82 Hz, 1H), 6.34 (d, J=7.57 Hz, 1H), 5.16 (bs, 2H).

후처리

  1. customfor 3 h
  2. filtrationThe crude mixture was filtered through a pad of Celite
  3. washwashing with MeOH
  4. concentrationconcentrated
  5. washThe column was washed with H20 and MeOH
  6. washThe columns were washed with H20 and MeOH
  7. additionEach of the columns containing product
  8. washwere washed separately with 10% concentrated NH4OH in MeOH
  9. customthe product collected in fractions
  10. concentrationThe collected fractions were concentrated

출처 및 근거

ORD 기록
ord-afce4a347362404db9eb4e796f71da2b
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09399651B2

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