N-(1H-Pyrrolo[2,3-c]pyridin-5-yl)acetamide → 1H-Pyrrolo(2,3-c)pyridin-5-amine

HRID 2393443ノート

反応式

HRID 2393443 の反応式
C([NH:4][C:5]1[CH:6]=[C:7]2[CH:13]=[CH:12][NH:11][C:8]2=[CH:9][N:10]=1)(=O)C>[OH-].[K+]>[NH3:4].[NH2:4][C:5]1[CH:6]=[C:7]2[CH:13]=[CH:12][NH:11][C:8]2=[CH:9][N:10]=1

参加物

4

反応物 1

HCID 18975304N-(1H-Pyrrolo[2,3-c]pyridin-5-yl)acetamide

生成物 2

HCID 222AmmoniaHCID 189753231H-Pyrrolo(2,3-c)pyridin-5-amine収率 164.8%

試薬・触媒・溶媒 1

HCID 14797Potassium Hydroxide溶媒

実験手順

5-Acetylamino-1H-pyrrolo[2,3-c]pyridine (0.61 g, 3.5 mmol) was heated at reflux in methanolic KOH (2M, 15 mL) under nitrogen for 8 hours. The solvent was evaporated in vacuo and the residue partitioned between dichloromethane (100 mL) and water (100 mL). The two layers were separated and the aqueous phase was extracted with n-butanol (3×100 mL). The combined organics were evaporated in vacuo and the residue chromatographed on silica eluting with 5 to 10% MeOH in DCM followed by a gradient of 90:10:1 to 80:20:1, DCM:MeOH:NH3 to give the title compound (0.384 g, 83%) as a red solid. mp 183°-186° C. 1H NMR (360 MHz, d6 -DMSO) δ 4.95 (2H, br s), 6.13-6.15 (1H, m), 6.52 (1H, s), 7.34-7.37 (1H, m), 8.17 (1H, s) and 10.90 (1H, br s).

後処理

  1. customThe solvent was evaporated in vacuo
  2. customthe residue partitioned between dichloromethane (100 mL) and water (100 mL)
  3. customThe two layers were separated
  4. extractionthe aqueous phase was extracted with n-butanol (3×100 mL)
  5. customThe combined organics were evaporated in vacuo
  6. customthe residue chromatographed on silica eluting with 5 to 10% MeOH in DCM

出典と根拠

ORDレコード
ord-db3e2375e2554a99b7713d64d71dbad8
出典データセット
uspto-grants-1998_09
特許番号
US05807857

反応ノート

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