Pyridine → N-[6-(5-Nitropyridin-2-yloxy)-2-phenylchroman-4-yl]-acetamide

HRID 31249Notes

Reaction equation

HRID 31249 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].Cl.[N+:9]([C:12]1[CH:13]=[CH:14][C:15]([O:18][C:19]2[CH:20]=[C:21]3[C:26](=[CH:27][CH:28]=2)[O:25][CH:24]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:23][CH:22]3[NH2:35])=[N:16][CH:17]=1)([O-:11])=[O:10].N1C=CC=CC=1>CN(C=O)C>[N+:9]([C:12]1[CH:13]=[CH:14][C:15]([O:18][C:19]2[CH:20]=[C:21]3[C:26](=[CH:27][CH:28]=2)[O:25][CH:24]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:23][CH:22]3[NH:35][C:1](=[O:3])[CH3:2])=[N:16][CH:17]=1)([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 17978520HCID 17978520, compound

Product 1

HCID 69254288N-[6-(5-Nitropyridin-2-yloxy)-2-phenylchroman-4-yl]-acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Acetic anhydride (60 μl) was added into a cooled solution of 6-(5-nitropyridin-2-yloxy)-2-phenylchroman-4-ylamine hydrochloride (100 mg) and pyridine (41 μl) in dry DMF. Resulting mixture was stirred for a further 20 hours at 0° C. Reaction was quenched with ice water and neutralised. Resulting mixture was extracted with dichloromethane, dried with Na2SO4 and evaporated. Mixture of diastereomers of N-[6-(5-nitropyridin-2-yloxy)-2-phenylchroman-4-yl]-acetamide was recrystallised from dichloromethane. (M)+=405 (24%), 301 (14%), 259 (100%), 242 (55%), 224 (96%).

Workup

  1. customResulting mixture
  2. customReaction
  3. customwas quenched with ice water
  4. customResulting mixture
  5. extractionwas extracted with dichloromethane
  6. dry with materialdried with Na2SO4
  7. customevaporated
  8. additionMixture of diastereomers of N-[6-(5-nitropyridin-2-yloxy)-2-phenylchroman-4-yl]-acetamide
  9. customwas recrystallised from dichloromethane

Sources & evidence

ORD record
ord-6a1c756233d841aeb35cbe75e9f6a61b
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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