N-Methylaniline → HCID 14390323, compound

HRID 621966Notes

Reaction equation

HRID 621966 reaction equation
C(Cl)(=O)C(Cl)=O.[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:22]([CH2:23][C:24]([OH:26])=O)[C:17]3=[N:18][CH:19]=[CH:20][CH:21]=[C:16]3[N:15]=2)=[CH:10][CH:9]=1.[CH3:27][NH:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(N(CC)CC)C>CN(C)C=O.O>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[N:22]([CH2:23][C:24]([N:28]([CH3:27])[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:26])[C:17]3=[N:18][CH:19]=[CH:20][CH:21]=[C:16]3[N:15]=2)=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 7515N-MethylanilineHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 143904574-chlorophenyl-3H-imidazo[4,5-b]pyridine-3-acetic acid

Product 1

HCID 14390323HCID 14390323, compoundYield 45.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

Under nitrogen atmosphere, oxalyl chloride (2.21 g, 0.0174 mole) was added slowly dropwise to a stirred and chilled (~10° C.) suspension of 2-(4-chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (5.0 g, 0.0174 mole) in 75 ml of dimethylformamide. After the addition was complete, the reaction was heated at 60° C. for 5 hrs. This acylchloride solution was added dropwise to a stirred and cooled (~10° C.) solution of N-methylaniline (2.02 g, 0.019 mole), triethylamine (1.88 g, 0.019 mole), and 74 ml of dimethylformamide. The reaction was stirred at room temperature overnight. The reaction mixture was poured into 200 ml of water and diluted with water until the cloud point. The mixture was seeded and refrigerated overnight. The solid was collected by filtration and dried under high vacuum. The solid was suspended in dilute sodium bicarbonate, collected by filtration, washed with water, and dried under high vacuum at 50° C. The solid was recrystallized from isopropyl alcohol-water, collected by filtration, washed with water, and dried under high vacuum first at 56° C., then at 98° C. for 2 days to give 3.0 g (45.7%) of crystals, mp 170°-171° C.

Workup

  1. temperaturechilled
  2. additionAfter the addition
  3. stirringa stirred
  4. stirringThe reaction was stirred at room temperature overnight
  5. filtrationThe solid was collected by filtration
  6. customdried under high vacuum
  7. filtrationcollected by filtration
  8. washwashed with water
  9. customdried under high vacuum at 50° C
  10. customThe solid was recrystallized from isopropyl alcohol-water
  11. filtrationcollected by filtration
  12. washwashed with water
  13. customdried under high vacuum first at 56° C.

Sources & evidence

ORD record
ord-0d77b87c493a4959a5968a291e170e34
Source dataset
uspto-grants-1989_04
Patent number
US04824951

Reaction notes

Loading…