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

HRID 1826724노트

반응식

HRID 1826724 반응식
[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

참가 물질

8

반응물 3

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

생성물 1

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

시약·촉매·용매 4

HCID 23994Zinc촉매HCID 176Acetic Acid용매2회HCID 702Ethanol용매HCID 6386tert-Butanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-60aac456ae5e4c0ea4cb52e3e5b69b9c
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07053086B2

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