Pyridine → HCID 59129340, compound

HRID 503354Notes

Reaction equation

HRID 503354 reaction equation
[CH3:1][C:2]1([C:5]#[C:6][C:7]2[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[CH:10][C:8]=2[NH2:9])[CH2:4][CH2:3]1.N1C=CC=CC=1.[C:23](Cl)(=[O:27])[CH2:24][CH2:25][CH3:26]>C(Cl)Cl>[CH3:1][C:2]1([C:5]#[C:6][C:7]2[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[CH:10][C:8]=2[NH:9][C:23](=[O:27])[CH2:24][CH2:25][CH3:26])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 8855Butyryl chlorideHCID 591295192-((1-Methylcyclopropyl)ethynyl)-4-nitroaniline

Product 1

HCID 59129340HCID 59129340, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-((1-methylcyclopropyl)ethynyl)-4-nitroaniline (220 mg, 1.0 mmol) and pyridine (160 mg, 2.0 mol) in CH2Cl2 (20 mL) was added butyryl chloride (140 mg, 1.3 mmol) at 0° C. The mixture was warmed to room temperature and stirred for 3 h. The mixture was poured into ice-water. The organic layer was separated and the aqueous phase was extracted with CH2Cl2 (30 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and evaporated under reduced pressure to obtain N-[2-(1-methyl-cyclopropyl-ethynyl)-4-nitro-phenyl]-butyramide (230 mg, 82%), which was directly used in the next step.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous phase was extracted with CH2Cl2 (30 mL×3)
  3. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-8689ece752064200ae17c3a2a4057707
Source dataset
uspto-grants-2010_08
Patent number
US07776905B2

Reaction notes

Loading…