Hydrochloric Acid → 2-(5-Bromopyridin-2-yl)acetic acid hydrochloride

HRID 1175629Notes

Reaction equation

HRID 1175629 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.[ClH:18]>>[ClH:18].[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 2

HCID 313Hydrochloric AcidHCID 574434985-(5-Bromopyridin-2(1H)-ylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 534036862-(5-Bromopyridin-2-yl)acetic acid hydrochloride

Procedure

5-(5-Bromopyridin-2(1H)-ylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione (example 42f) (3.55 g, 11.87 mmol) was suspended in conc. HCl (55 mL) and refluxed for 3 h. The solution was concentrated under reduced pressure and a residue was triturated with EtOH to provide white crystals that were filtered off and washed with EtOH (2.34 g, 78%). 1H NMR (400 MHz, dMSO): δ 3.81 (s, 2H), 7.44-7.46 (d, 1H), 8.12-8.15 (dd, 1H), 8.70-8.71 (d, 1H), 11.30 (bs, 1H); MS+H (218).

Workup

  1. temperaturerefluxed for 3 h
  2. concentrationThe solution was concentrated under reduced pressure
  3. customa residue was triturated with EtOH
  4. customto provide white crystals that
  5. filtrationwere filtered off
  6. washwashed with EtOH (2.34 g, 78%)

Sources & evidence

ORD record
ord-7c83d041225f4a6380986fd816c94a49
Source dataset
uspto-grants-2010_11
Patent number
US07842324B2

Reaction notes

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