Water → 5-(2-oxo-2,3-dihydro-1H-indol-4-yl)-nicotinic acid

HRID 988143ノート

反応式

HRID 988143 の反応式
[Br-].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH:22]1[C:30]2[C:25](=[C:26]([C:31]3[CH:32]=[N:33][CH:34]=[C:35]([CH:39]=3)[C:36]([OH:38])=[O:37])[CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23]1.[OH2:40]>CC(O)(C)C.C(O)C.C(O)(=O)C.[Zn]>[O:40]=[C:23]1[CH2:24][C:25]2[C:30](=[CH:29][CH:28]=[CH:27][C:26]=2[C:31]2[CH:32]=[N:33][CH:34]=[C:35]([CH:39]=2)[C:36]([OH:38])=[O:37])[NH:22]1

参加物

8

反応物 3

HCID 962WaterHCID 21124087PyridiniumtribromideHCID 221354775-(1H-indol-4-yl)-nicotinic acid

生成物 1

HCID 221353975-(2-oxo-2,3-dihydro-1H-indol-4-yl)-nicotinic acid収率 98%

試薬・触媒・溶媒 4

HCID 23994Zinc触媒HCID 176Acetic Acid溶媒2 回HCID 702Ethanol溶媒HCID 6386tert-Butanol溶媒

実験手順

Pyridinium tribromide (90% (Aldrich), 9.8 g, 27.6 mmol) was added portion-wise over 10 minutes to a suspension of 5-(1H-indol-4-yl)-nicotinic acid (2.2 g, 9.2 mmol) in 2-methyl-2-propanol (54 mL), ethanol (36 mL) and acetic acid (108 mL). The mixture was stirred at room temperature for 2 hours and then acetic acid (10 mL) was added. After stirring for an additional hour, water (0.5 mL) and zinc dust (6 g, 92 mmol) were added and stirring was continued for another hour. Residual zinc dust was filtered and washed with methanol. The filtrate was concentrated and the syrupy residue was stirred in water (300 mL) overnight. The solid which formed was filtered, washed with water to remove zinc and pyridine salts and dried under high vacuum to give 2.3 g (98%) of 5-(2-oxo-2,3-dihydro-1H-indol-4-yl)-nicotinic acid.

後処理

  1. stirringAfter stirring for an additional hour
  2. stirringstirring
  3. waitwas continued for another hour
  4. filtrationResidual zinc dust was filtered
  5. washwashed with methanol
  6. concentrationThe filtrate was concentrated
  7. stirringthe syrupy residue was stirred in water (300 mL) overnight
  8. customThe solid which formed
  9. filtrationwas filtered
  10. washwashed with water
  11. customto remove zinc and pyridine salts
  12. customdried under high vacuum

出典と根拠

ORDレコード
ord-4f0f685df7fb4da1ba4fe72076fc25ec
出典データセット
uspto-grants-2003_10
特許番号
US06635640B2

反応ノート

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