2,6-Dimethylaniline → HCID 18419454, compound

HRID 1074147Notes

Reaction equation

HRID 1074147 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.C(N(CC)CC)C.ClC(OCC)=O.[CH3:24][C:25]1[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[C:26]=1[NH2:27]>CC(C)=O.O>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:6]([NH:27][C:26]2[C:28]([CH3:32])=[CH:29][CH:30]=[CH:31][C:25]=2[CH3:24])=[O:8])=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 68962,6-DimethylanilineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 792226-Chloronicotinic acid

Product 1

HCID 18419454HCID 18419454, compoundYield 73.7%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent3×HCID 962WaterSolvent

Conditions

Temperature
-10 °C

Procedure

A slurry of 25 g of 6-chloronicotinic acid in approximately 300 ml of acetone was treated with 22.6 ml of triethylamine. The reaction mixture was cooled to approximately -10° C. by means of an external ice/methanol bath. A solution of 15.5 ml of ethyl chloroformate in acetone was added to the mixture at a rate to maintain the temperature below 0° C. After stirring with the cold bath for 2 hours, a solution of 38.5 g of 2,6-dimethylaniline in approximately 150 ml of acetone was added while maintaining the temperature below 0° C. After the addition was complete, the mixture was allowed to warm to room temperature overnight. The mixture was poured into water and extracted into ethyl acetate. The organic layer was washed with water, dilute hydrochloric acid, water, a dilute sodium bicarbonate solution, water (twice), and a saturated sodium chloride solution. The organic solution was dried over sodium sulfate and concentrated in vacuo to provide 30.5 g of a solid. Crystallization from methanol/water provided 14.6 g of the desired title product, m.p. 165°-166° C.

Workup

  1. temperatureto maintain the temperature below 0° C
  2. temperaturewhile maintaining the temperature below 0° C
  3. additionAfter the addition
  4. temperatureto warm to room temperature overnight
  5. extractionextracted into ethyl acetate
  6. washThe organic layer was washed with water, dilute hydrochloric acid, water
  7. dry with materialThe organic solution was dried over sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-04385f9cc76a40ab98b3904d5e78b372
Source dataset
uspto-grants-1990_11
Patent number
US04973597

Reaction notes

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