Hydrochloric Acid → 4-chloro-2,5-difluoro-N-(2-methoxy-4-pyridyl)benzamide

HRID 2170425Notes

Reaction equation

HRID 2170425 reaction equation
[Cl:1][C:2]1[C:10]([F:11])=[CH:9][C:5]([C:6](Cl)=[O:7])=[C:4]([F:12])[CH:3]=1.[CH3:13][O:14][C:15]1[CH:20]=[C:19]([NH2:21])[CH:18]=[CH:17][N:16]=1.N1C=CC=CC=1.Cl>ClCCl>[Cl:1][C:2]1[C:10]([F:11])=[CH:9][C:5]([C:6]([NH:21][C:19]2[CH:18]=[CH:17][N:16]=[C:15]([O:14][CH3:13])[CH:20]=2)=[O:7])=[C:4]([F:12])[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 2808912-Methoxypyridin-4-amineHCID 27364984-Chloro-2,5-difluorobenzoyl chloride

Product 1

HCID 867284804-chloro-2,5-difluoro-N-(2-methoxy-4-pyridyl)benzamideYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-chloro-2,5-difluoro-benzoyl chloride (5 g, 23.70 mmol) in dichloromethane (25 mL) was added dropwise to a mixture of 2-methoxypyridin-4-amine (2.94 g, 23.70 mmol), pyridine (5.75 mL, 71.10 mmol) and dichloromethane (100.0 mL) at 0° C. The mixture was allowed to warm to room temperature and was stirred at that temperature for 43 hours. The mixture was poured into 1N HCl (50 mL). The mixture was filtered using dichloromethane and the solid was isolated. The solid was dried under vacuum to yield 4-chloro-2,5-difluoro-N-(2-methoxy-4-pyridyl)benzamide (6.2 g, 88%) as a pink solid. 1H NMR (400 MHz, DMSO-d6) δ 10.89 (s, 1H), 8.16-8.05 (m, 1H), 7.97-7.75 (m, 2H), 7.29-7.15 (m, 2H), 3.85 (s, 3H) ppm. ESI-MS m/z calc. 298.03. found 299.3 (M+1)+; Retention time: 1.43 minutes (3 minutes run).

Workup

  1. filtrationThe mixture was filtered
  2. customthe solid was isolated
  3. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-c98dc008c88f4377a3cedb486e80c191
Source dataset
uspto-grants-2015_06
Patent number
US09051270B2

Reaction notes

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