Dichloromethane → HCID 86632959, compound

HRID 249716Notes

Reaction equation

HRID 249716 reaction equation
O[C:2]1C(C(O)=O)=[CH:6][N:5]=[C:4]([CH3:11])[CH:3]=1.[C:12](Cl)(=O)[C:13]([Cl:15])=[O:14].C(Cl)[Cl:19]>CN(C=O)C>[Cl:19][C:2]1[C:12]([C:13]([Cl:15])=[O:14])=[CH:6][N:5]=[C:4]([CH3:11])[CH:3]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 178429106HCID 178429106, compound

Product 1

HCID 86632959HCID 86632959, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

4-Hydroxy-6-methylnicotinic acid (5 g) was dissolved in abs. DCM (30 ml) and treated with 10 drops of DMF. Oxalyl chloride (15 ml) was carefully added dropwise to this mixture. After stirring for four hours and allowing to stand overnight, the solvent was stripped off and for further drying the mixture was attached to the high vacuum. The 4-chloro-6-methylnicotinoyl chloride obtained (8 g) was dissolved in abs. DCM (160 ml). After cooling to 0° C., a 40% strength methanolic methylamine solution (66 ml) was added dropwise in the course of 15 min. After removal of the cooling, the mixture was additionally stirred at RT for 2 h. After addition of water (150 ml), it was extracted with DCM (three times). The combined organic phases were dried over sodium sulfate, filtered and concentrated. 4.4 g of the desired compound were obtained.

Workup

  1. waitto stand overnight
  2. customfor further drying the mixture

Sources & evidence

ORD record
ord-4357688a2b8041d68cd798610770819f
Source dataset
uspto-grants-2011_01
Patent number
US07863269B2

Reaction notes

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