Pyridine → HCID 21996739, compound

HRID 1978050Notes

Reaction equation

HRID 1978050 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([OH:13])=O)=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:14]([OH:16])=O.[CH:17]1([NH2:22])[CH2:21][CH2:20][CH2:19][CH2:18]1.P(OC1C=CC=CC=1)(OC1C=CC=CC=1)OC1C=CC=CC=1.[N:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>C(O)(C)C.O.CN1CCCC1=O>[CH:17]1([NH:22][C:11]([C:7]2[CH:8]=[CH:9][C:10]3[C:5](=[CH:4][CH:3]=[C:2]([C:14]([NH:45][CH:50]4[CH2:49][CH2:48][CH2:47][CH2:46]4)=[O:16])[CH:1]=3)[CH:6]=2)=[O:13])[CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

7

Reactant 4

HCID 1049PyridineHCID 2906CyclopentylamineHCID 7540Triphenyl phosphiteHCID 143572,6-Naphthalenedicarboxylic acid

Product 1

HCID 21996739HCID 21996739, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 13387N-methyl-2-pyrrolidoneSolventHCID 21889133Propan-2-ol--water (1/1)Solvent

Procedure

A 300 ml four-necked flask equipped with a stirrer, thermometer, condenser and gas inlet was charged with 6.48 g (0.03 mole) of 2,6-naphthalenedicarboxylic acid, 5.61 g (0.066 mole) of cyclopentylamine, 20.46 g (0.066 mol) of triphenyl phosphite, 25 g of pyridine and 100 g of N-methylpyrrolidone, and the reaction was carried out in a nitrogen gas atmosphere at 100° C. for 3 hours, with stirring. After cooling, the reaction mixture was poured in 700 ml of isopropyl alcohol/water (1:1) for reprecipitation and washing. The mixture was stirred for 2 hours and the precipitate was then recovered by filtration and dried under reduced pressure at 110° C. to provide 9.03 g (yield 86%) of N,N′-dicyclopentyl-2,6-naphthalenedicarboxamide. This compound was a white powder melting at 375.4° C. (decomp.). The elemental analysis and characteristic infrared absorptions are shown in Table 1.

Workup

  1. customA 300 ml four-necked flask equipped with a stirrer
  2. temperatureAfter cooling
  3. washwashing
  4. stirringThe mixture was stirred for 2 hours
  5. filtrationthe precipitate was then recovered by filtration
  6. customdried under reduced pressure at 110° C.

Sources & evidence

ORD record
ord-3a01237fab1d4e7483aae54d4d6e9e7c
Source dataset
uspto-grants-2001_05
Patent number
US06235823B1

Reaction notes

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