Pimelic Acid → HCID 90388860, compound

HRID 2276711Notes

Reaction equation

HRID 2276711 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:8])[CH:5]=[N:6][CH:7]=1.[C:9](O)(=[O:18])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16].[OH-].[Na+]>>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:18])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])[CH:5]=[N:6][CH:7]=1

Participants

4

Reactant 3

HCID 385Pimelic AcidHCID 14798Sodium HydroxideHCID 8176813-Amino-5-bromopyridine

Product 1

HCID 90388860HCID 90388860, compoundYield 66.2%

Conditions

Temperature
130 °C

Procedure

The mixture of 5-bromopyridin-3-amine (2.0 g, 11.6 mmol) and heptanedioic acid (2.22 g, 13.9 mmol) was heated and stirred at 130° C. for 8 h. After the reaction was completed, the solution was cooled to 50° C. and added to NaOH solution. The mixture was filtered. The filtration was extracted with EtOAc (50 mL×3) and concentrated HCl was added until pH=1. The solid was collected to give the product as a yellow solid 2.42 g (yield 66.2%).

Workup

  1. temperaturewas heated
  2. temperaturethe solution was cooled to 50° C.
  3. filtrationThe mixture was filtered
  4. filtrationThe filtration
  5. extractionwas extracted with EtOAc (50 mL×3) and concentrated HCl
  6. additionwas added until pH=1
  7. customThe solid was collected

Sources & evidence

ORD record
ord-c08e6e72ec9c49cebb10337019cba9bf
Source dataset
uspto-grants-2015_09
Patent number
US09133105B2

Reaction notes

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