5-(5-Bromopyridin-2(1H)-ylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione → (5-Bromopyridin-2-yl)acetic acid

HRID 533505Notes

Reaction equation

HRID 533505 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](=[C:8]2C(=O)OC(C)(C)[O:10][C:9]2=[O:17])[NH:6][CH:7]=1>Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([OH:17])=[O:10])=[N:6][CH:7]=1

Participants

3

Reactant 1

HCID 574434985-(5-Bromopyridin-2(1H)-ylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 46238459(5-Bromopyridin-2-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 5-(5-bromopyridin-2(1H)-ylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione (3) (40.0 g, 133.3 mmol) in HCl (30%, 400 mL) was heated gently to reflux, and was refluxed for 2 h. The solvent was removed in vacuo and the residue (29.75 g) was used in the next step without further purification. 1H-NMR (CDCl3, 300 MHz): δ 3.79 (s, 2H, CH2), 7.41 (d, 1H, ArH), 8.08 (dd, 1H, ArH), 8.66 (d, 1H, ArH).

Workup

  1. temperatureto reflux
  2. temperaturewas refluxed for 2 h
  3. customThe solvent was removed in vacuo
  4. customthe residue (29.75 g) was used in the next step without further purification

Sources & evidence

ORD record
ord-ed9b94004346481598f2462e27f3012f
Source dataset
uspto-grants-2014_10
Patent number
US08853258B2

Reaction notes

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