Dimethylformamide → HCID 58149915, compound

HRID 2192489Notes

Reaction equation

HRID 2192489 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[Cl:7][C:8]1[CH:9]=C(C(O)=O)[CH:11]=[N:12][C:13]=1[O:14][CH:15]([CH3:17])[CH3:16].CN(C)C=O>ClCCl>[Cl:7][C:8]1[CH:9]=[C:1]([C:2]([Cl:4])=[O:3])[CH:11]=[N:12][C:13]=1[O:14][CH:15]([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 180705825-Chloro-6-isopropoxynicotinic acid

Product 1

HCID 58149915HCID 58149915, compoundYield 131.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (0.07 ml, 0.800 mmol) was added to a stirred solution of 5-chloro-6-[(1-methylethyl)oxy]-3-pyridinecarboxylic acid (WO 2008074820; 86 mg, 0.40 mmol) in dichloromethane (DCM) (2 ml) containing N,N-dimethylformamide (DMF) (0.02 ml) at 0° under nitrogen and the mixture was allowed to warm to room temperature with stirring overnight. The solvent was evaporated in vacuo to give a yellow gum (123 mg) which was used in the subsequent reaction (D53) without further purification

Workup

  1. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-08bd929818c54fb88508393a15fb16e6
Source dataset
uspto-grants-2012_12
Patent number
US08329730B2

Reaction notes

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