4-Nitrobenzimidazole → 7-Aminobenzimidazole

HRID 571062ノート

反応式

HRID 571062 の反応式
[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

参加物

4

反応物 1

HCID 1609494-Nitrobenzimidazole

生成物 1

HCID 203297-Aminobenzimidazole

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 176Acetic Acid溶媒

実験手順

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 H2O 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 H2O 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, 1 H), 7.98 (s, 1 H), 6.87 (t, J=7.81 Hz, 1 H), 6.72 (d, J=7.82 Hz, 1 H), 6.34 (d, J=7.57 Hz, 1 H), 5.16 (bs, 2 H).

後処理

  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 H2O and MeOH
  6. washThe columns were washed with H2O 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

出典と根拠

ORDレコード
ord-551cd3c3d05244c39e7e2d209f05d0a8
出典データセット
uspto-grants-2015_05
特許番号
US09024032B2

反応ノート

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