Sodium Hydroxide → (4-Nitropyridin-2-yl)methanol

HRID 600263Notes

Reaction equation

HRID 600263 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][N:7]=[C:6]([CH2:10][O:11]C(=O)C)[CH:5]=1)([O-:3])=[O:2].[OH-].[Na+]>CO>[N+:1]([C:4]1[CH:9]=[CH:8][N:7]=[C:6]([CH2:10][OH:11])[CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14761430(4-Nitropyridin-2-yl)methyl acetate

Product 1

HCID 14761455(4-Nitropyridin-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of acetic acid 4-nitro-pyridin-2-ylmethyl ester (16)(0.49 g, 2.5 mmol) in methanol (5 mL), was added a solution of sodium hydroxide (2N, 1.6 mL) and the reaction was stirred for 30 minutes and then concentrated in vacuo. The residue was diluted with water (10 mL) and extracted with ethyl acetate (2×10 mL). The combined extracts were washed with brine (10 mL) and concentrated in vacuo to afford a crude oil which solidified upon standing. Single peak in LC-MS analysis, (0.13 g 33%); m/z (LC-MS, ESP), RT=2.67 mins, (M+H) 155.

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with water (10 mL)
  3. extractionextracted with ethyl acetate (2×10 mL)
  4. washThe combined extracts were washed with brine (10 mL)
  5. concentrationconcentrated in vacuo
  6. customto afford a crude oil which

Sources & evidence

ORD record
ord-5b7dff31fb944675a071fa21c386ddaf
Source dataset
uspto-grants-2011_03
Patent number
US07902193B2

Reaction notes

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