Hydrochloric Acid → HCID 53939129, compound

HRID 1680451Notes

Reaction equation

HRID 1680451 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=2)=[CH:7][N:6]=1)=[O:4].[H-].[Na+].[Cl:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH2:26]Cl.Cl>CN(C)C=O>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]([CH2:26][C:25]2[CH:28]=[CH:29][CH:30]=[C:23]([Cl:22])[CH:24]=2)[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=2)=[CH:7][N:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 12103m,alpha-DichlorotolueneHCID 24758Sodium hydrideHCID 12640161HCID 12640161, compound

Product 1

HCID 53939129HCID 53939129, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To the solution of 1.38 g of 5-(m-chlorobenzylamino)-pyridine-2-carboxylic acid methyl ester in 15 ml of dimethylformamide, 0.12 g of sodium hydride in 2 ml of dimethylformamide are added and the mixture is stirred several minutes. Then 0.97 g of m-chlorobenzyl chloride are added and the mixture is stirred at room temperature for 18 hours. It is made acidic with diluted hydrochloric acid and extracted with diethyl ether. The extract is washed with 10% aqueous potassium bicarbonate and water, dried and evaporated, to yield the 5-[di-(m-chlorobenzyl)-amino]-pyridine-2-carboxylic acid methyl ester.

Workup

  1. stirringthe mixture is stirred at room temperature for 18 hours
  2. extractionextracted with diethyl ether
  3. washThe extract is washed with 10% aqueous potassium bicarbonate and water
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-9329fb0c09ef47189a749c460efacfd1
Source dataset
uspto-grants-1981_06
Patent number
US04273779

Reaction notes

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