Lithium Chloride → HCID 117771679, compound

HRID 2201527Notes

Reaction equation

HRID 2201527 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[O:9])[C:5]([O:19]C)=[CH:4][CH:3]=1.[Cl-].[Li+]>CN(C=O)C>[Br:1][C:2]1[N:7]=[C:6]([C:8]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[O:9])[C:5]([OH:19])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 433294Lithium ChlorideHCID 117771406HCID 117771406, compound

Product 1

HCID 117771679HCID 117771679, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of 6-bromo-N-(4-chlorobenzyl)-3-methoxypicolinamide (800 mg, 2.25 mmol) in DMF (10 mL) was added lithium chloride (954 mg, 22.5 mmol), and the mixture was heated at 130° C. for 16 h. The mixture was concentrated in vacuo and the residue was suspended in water. Finally, the crude 6-bromo-N-(4-chlorobenzyl)-3-hydroxypicolinamide (700 mg, yield: 91%) was obtained by filtration. 1H-NMR (DMSO-d6, 400 MHz) δ 12.47 (br s, 1H), 9.67 (s, 1H), 7.71 (d, J=8.8 Hz, 1H), 7.34˜7.42 (m, 5H), 4.46 (d, J=6.0 Hz, 2H). MS (M+H)+: 341/343.

Workup

  1. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-14ecccb627184f3eade86e8baf98e61c
Source dataset
uspto-grants-2016_06
Patent number
US09364482B2

Reaction notes

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