Ammonia → 2-(6-Bromopyridin-2-yl)-2-hydroxyacetamide

HRID 1500201Notes

Reaction equation

HRID 1500201 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH:8]([OH:13])[C:9](OC)=[O:10])[CH:5]=[CH:4][CH:3]=1.[NH4+:14].[Cl-].N>CO>[Br:1][C:2]1[N:7]=[C:6]([CH:8]([OH:13])[C:9]([NH2:14])=[O:10])[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 59825086Methyl 2-(6-bromopyridin-2-yl)-2-hydroxyacetate

Product 1

HCID 898154332-(6-Bromopyridin-2-yl)-2-hydroxyacetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 2-(6-bromopyridin-2-yl)-2-hydroxyacetate (0.5, g, 2.03 mmol), NH4Cl (0.1, g) and NH3, (4N in MeOH) was shaken at room temperature over night. The solvent was removed under vacuum then added water (5, mL) and CHCl3, (20, mL) The organic layer was concentrated and purified by chromatographed over silica gel with 50% EtOAc in hexanes to yield 2-(6-bromopyridin-2-yl)-2-hydroxyacetamide as a yellow solid (0.2, g, 16%). 1H NMR (600, MHz, DMSO-d6) 7.77, (1H, dd, J=7.8, & 8.4, Hz), 7.58, (1H, d, J=8.4, Hz), 7.51-7.52, (2H, m), 7.35, (1 H, s), 6.23, (1H, d, J=0.5, Hz, —OH), 4.91 (1H, d, J=0.6, Hz).

Workup

  1. customThe solvent was removed under vacuum
  2. concentrationadded water (5, mL) and CHCl3, (20, mL) The organic layer was concentrated
  3. custompurified
  4. customby chromatographed over silica gel with 50% EtOAc in hexanes

Sources & evidence

ORD record
ord-eca519a3a8374bc2b3b91d67ec1a8cce
Source dataset
uspto-grants-2015_12
Patent number
US09206127B2

Reaction notes

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