Methanol → (RS) methyl 3-{5-[2-(3-hydroxy-4-nitrophenyl)-acetylamino]-pyridin-2-yl}-butanoate

HRID 49721Notes

Reaction equation

HRID 49721 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:11][C:12]([NH:14][C:15]2[CH:16]=[CH:17][C:18]([CH:21]([CH3:26])[CH2:22][C:23]([OH:25])=[O:24])=[N:19][CH:20]=2)=[O:13])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].S(=O)(=O)(O)O.[CH3:32]O>>[OH:1][C:2]1[CH:3]=[C:4]([CH2:11][C:12]([NH:14][C:15]2[CH:16]=[CH:17][C:18]([CH:21]([CH3:26])[CH2:22][C:23]([O:25][CH3:32])=[O:24])=[N:19][CH:20]=2)=[O:13])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 20636575HCID 20636575, compound

Product 1

HCID 17946659(RS) methyl 3-{5-[2-(3-hydroxy-4-nitrophenyl)-acetylamino]-pyridin-2-yl}-butanoate

Procedure

(RS) 3-{5-[2-(3-hydroxy-4-nitrophenyl)-acetylamino]-pyridin-2-yl}-butanoic acid (2.1 g, Reference Example 26) in methanol (80 mL) was treated with concentrated sulphuric acid (0.5 mL). The mixture was heated at reflux temperature for 24 hours, then cooled, then concentrated to low volume and then diluted with ethyl acetate. This solution was washed with 5% aqueous sodium bicarbonate, then with water, then dried over magnesium sulphate and then evaporated to give the title compound (2.0 g) as an oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux temperature for 24 hours
  3. temperaturecooled
  4. concentrationconcentrated to low volume
  5. additiondiluted with ethyl acetate
  6. washThis solution was washed with 5% aqueous sodium bicarbonate
  7. dry with materialwith water, then dried over magnesium sulphate
  8. customevaporated

Sources & evidence

ORD record
ord-a0df956f6aef47f38a57cfbde85db658
Source dataset
uspto-grants-2004_03
Patent number
US06706738B2

Reaction notes

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