2,4,6-Trimethylaniline → HCID 22105937, compound

HRID 1456370Notes

Reaction equation

HRID 1456370 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[N:9][CH:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])=[C:4](C(O)=O)[C:3]1=[O:22].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:30])C=CC=CC=1.C([N:42]([CH2:45]C)CC)C.[CH3:47][C:48]1[CH:54]=[C:53]([CH3:55])[CH:52]=[C:51]([CH3:56])[C:49]=1[NH2:50]>CN(C)C=O.C(OCC)(=O)C>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[N:9][CH:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])=[C:4]([NH:42][C:45]([NH:50][C:49]2[C:51]([CH3:56])=[CH:52][C:53]([CH3:55])=[CH:54][C:48]=2[CH3:47])=[O:30])[C:3]1=[O:22]

Participants

7

Reactant 4

HCID 69132,4,6-TrimethylanilineHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 22106030HCID 22106030, compound

Product 1

HCID 22105937HCID 22105937, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-methyl-4-(2-chlorophenyl)-1,2-dihydro-2-oxo-1,7-naphthyridine-3-carboxylic acid (315 mg, 1 mmol), diphenylphosphoryl azide (330 mg, 1.2 mmol) and triethylamine (101 mg, 1 mmol) in N,N-dimethylformamide (DMF, 5 ml) was stirred at room temperature for 0.5 hour, and stirred at 80°-90° C. for 0.5 hour. After allowed to stand for cooling, to the mixture was added 2,4,6-trimethylaniline (162 mg, 1.2 mmol), and the mixture was stirred at room temperature for 0.5 hour, and then stirred at 80-90° C. for two hours. After allowed to stand for cooling, the mixture was diluted with ethyl acetate, washed with water, washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting solid was recrystallized from ethanol to give the title compound (350 mg, 0.78 mmol) as a colorless crystal.

Workup

  1. temperaturefor cooling, to the mixture
  2. stirringthe mixture was stirred at room temperature for 0.5 hour
  3. stirringstirred at 80-90° C. for two hours
  4. temperaturefor cooling
  5. washwashed with water
  6. washwashed with a saturated aqueous sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-a5fe2fc100ea4a879ecd0e13afef8df7
Source dataset
uspto-grants-1998_12
Patent number
US05843957

Reaction notes

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