Hydrochloric Acid → HCID 90011309、化合物

HRID 1054912ノート

反応式

HRID 1054912 の反応式
[CH3:1][O:2][C:3](=[O:16])[CH2:4][O:5][C:6]1[C:7]([N+:13]([O-])=O)=[N:8][C:9]([Br:12])=[CH:10][CH:11]=1.Cl.C(=O)(O)[O-].[Na+]>CO.[Fe]>[CH3:1][O:2][C:3](=[O:16])[CH2:4][O:5][C:6]1[C:7]([NH2:13])=[N:8][C:9]([Br:12])=[CH:10][CH:11]=1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 90011186(6-Bromo-2-nitropyridin-3-yloxy)acetic acid methyl ester

生成物 1

HCID 90011309HCID 90011309、化合物

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 887Methanol溶媒

反応条件

温度
60 °C

実験手順

(6-Bromo-2-nitropyridin-3-yloxy)acetic acid methyl ester (10.9 g, 37.5 mmol) was dissolved in methanol (90 mL). Concentrated HCl (10 mL) was then added followed by iron (6.4 g, 110 mmol). The reaction mixture was stirred at 60° C. for 1 hour. Then, the reaction mixture was cooled to room temperature and neutralized with solid sodium bicarbonate. The insoluble iron salts were removed by centrifugation. Silica gel was then added to the supernatant and the solvents were removed under reduced pressure. The resulting crude material was purified by column chromatography (SiO2, EtOAc/hexanes) to give (2-amino-6-bromopyridin-3-yloxy)acetic acid methyl ester. Yield 4.0 g (15 mmol, 40%). LCMS (ESI): calc. C8H9BrN2O3=260, 262; obs. M+H=261, 263.

後処理

  1. customThe insoluble iron salts were removed by centrifugation
  2. additionSilica gel was then added to the supernatant
  3. customthe solvents were removed under reduced pressure
  4. customThe resulting crude material was purified by column chromatography (SiO2, EtOAc/hexanes)

出典と根拠

ORDレコード
ord-5e0bf88fb9bb48c591a353ace90aeff0
出典データセット
uspto-grants-2016_07
特許番号
US09394315B2

反応ノート

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