N-methyl-2-pyrrolidone → HCID 85997292, compound

HRID 2262433Notes

Reaction equation

HRID 2262433 reaction equation
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH2:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN1CCCC1=O.[Br:22][C:23]1[N:28]=[C:27]([C:29](Cl)=[O:30])[CH:26]=[CH:25][CH:24]=1.CN1CCCC1=O>O>[Br:22][C:23]1[N:28]=[C:27]([C:29]([NH:14][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[NH:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[O:30])[CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 68297N-Phenyl-o-phenylenediamineHCID 86606187HCID 86606187, compound

Product 1

HCID 85997292HCID 85997292, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Dissolving 4.4 g (24 mmol) of N-phenyl-1,2-phenylenediamine into 30 milliliter of N-methylpyrrolidone, 10 milliliter of 6-bromo picolinoyl chloride/N-methylpyrrolidone was dropped under cooling with ice. The resultant solution was further stirred at room temperature for 4 hours. After completion of the reaction, the reacted solution was poured into 400 milliliter of water and the resultant solution was further stirred. The resultant solids were separated by filtration, washed with water and methanol, dried under reduced pressure, thereby obtaining 4.5 g of 6-bromo-2′-(N-phenylamino)-picoline anilide (yield: 49%).

Workup

  1. additionwas dropped
  2. temperatureunder cooling with ice
  3. customAfter completion of the reaction
  4. customThe resultant solids were separated by filtration
  5. washwashed with water and methanol
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-594f166620494ff199fce391dc69019c
Source dataset
uspto-grants-2010_12
Patent number
US07851071B2

Reaction notes

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