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

HRID 1500201ノート

反応式

HRID 1500201 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-eca519a3a8374bc2b3b91d67ec1a8cce
出典データセット
uspto-grants-2015_12
特許番号
US09206127B2

反応ノート

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