Ammonium Chloride → (1-Tosyl-1H-indol-4-YL)methanamine

HRID 475184

反応式

HRID 475184 の反応式
[S:1]([N:11]1[C:19]2[CH:18]=[CH:17][CH:16]=[C:15]([CH:20]=[N:21]O)[C:14]=2[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[NH4+].[Cl-]>CCO.[Zn]>[S:1]([N:11]1[C:19]2[C:14](=[C:15]([CH2:20][NH2:21])[CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12]1)([C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=1)(=[O:2])=[O:3]

参加物

5

反応物 2

HCID 25517Ammonium ChlorideHCID 866947201-tosyl-1H-indole-4-carbaldehyde oxime

生成物 1

HCID 67262154(1-Tosyl-1H-indol-4-YL)methanamine収率 100%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 702Ethanol溶媒

実験手順

To a solution of 44 (620 mg, 2 mmol) in EtOH (15 mL) was added zinc powder (320 mg, 5.0 mmol) and NH4Cl (0.53 g, 10 mmol). The reaction mixture was heated at reflux overnight, filtered and the filtrate was concentrated to dryness. The residue was diluted with DCM (100 mL) and water (20 mL). The organic layer was separated, dried (MgSO4), filtered and concentrated to afford 600 mg (100%) of (1-tosyl-1H-indol-4-yl)methanamine (46) as yellow syrup: MS (ESI) m/z=284.1 [M−15]+.

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated to dryness
  5. additionThe residue was diluted with DCM (100 mL) and water (20 mL)
  6. customThe organic layer was separated
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-2ed973f2124e4f32b3d4ad3f5aa61fe1
出典データセット
uspto-grants-2014_01
特許番号
US08637537B2

関連ノート

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