2-Aminopyridine → HCID 22497154, compound

HRID 1816020Notes

Reaction equation

[Cl:1][CH:2]1[CH:12]=[CH:11][CH:5]2[C:6]([O:8][C:9](=[O:10])[CH:4]2[CH2:3]1)=O.[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1>>[N:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[N:13]1[C:9](=[O:10])[CH:4]2[CH2:3][CH:2]([Cl:1])[CH:12]=[CH:11][CH:5]2[C:6]1=[O:8]

Participants

Reactant 2

HCID 104392-Aminopyridine

HCID 54187688HCID 54187688, compound

Product 1

HCID 22497154HCID 22497154, compoundYield 97%

Conditions

Temperature: 130 °C

Procedure

119.5 grams (0.64 moles) of 4-chlorotetrahydrophthalic anhydride and 94.1 grams (0.64 moles) of 2-aminopyridine were added to a 500-mL, 3-necked, round-bottomed flask equipped with a Dean-Stark trap topped with a condenser, a nitrogen outlet, means for maintaining a mild sweep of nitrogen over the reaction mixture, and a magnetic stir. The material was heated to 130° C. with an externally heated oil bath to provide an easily stirred melt. The reaction was heated to 175° C. for a 45 minute period. The water of imidization collected in the Dean-Stark trap. The reaction was then heated to 220 to 225° C. for 2.5 hours and the resulting amber material was transferred into a clean glass jar. The crude material was recovered in 97% yield. HPLC analysis of the crude material indicated >98% purity of the desired compound.

Workup

custom3-necked, round-bottomed flask equipped with a Dean-Stark trap
customtopped with a condenser, a nitrogen outlet
temperaturefor maintaining a mild sweep of nitrogen over the reaction mixture
customto provide
temperatureThe reaction was heated to 175° C. for a 45 minute period
customThe water of imidization collected in the Dean-Stark trap
temperatureThe reaction was then heated to 220 to 225° C. for 2.5 hours
customThe crude material was recovered in 97% yield

Sources & evidence

ORD record: ord-d24aff7fabad4e76a4a485272adf53f2
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06881815B2

Reaction notes

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