Hydrochloric Acid → 1-(Pyrazin-2-yl)cyclopropane-1-carboxylic acid

HRID 1672034ノート

反応式

HRID 1672034 の反応式
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]1([C:10]#N)[CH2:9][CH2:8]1.[OH-:12].[Na+].Cl.C[OH:16]>>[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]1([C:10]([OH:16])=[O:12])[CH2:9][CH2:8]1

参加物

5

反応物 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 584311071-(Pyrazin-2-YL)cyclopropanecarbonitrile

生成物 1

HCID 584310521-(Pyrazin-2-yl)cyclopropane-1-carboxylic acid

反応条件

温度
75 °C

実験手順

1-(Pyrazin-2-yl)cyclopropanecarbonitrile (0.25 g, 1.72 mmol, 1 eq) was dissolved in MeOH (5 ml) and NaOH solution (20 wt % in water, 2.0 ml) was added via syringe in one portion. The orange mixture was heated to 75° C. for 22 h., cooled to room temperature, and acidified to pH 2-3 with 6N HCl. The mixture was filtered through a pad of celite with MeOH wash and the filtrate was concentrated. The residue was suspended in ethyl acetate, dried with Na2SO4, filtered and concentrated to give the product as an orange solid. Yield: 0.18 g (64%) 1H NMR (400 MHz, DMSO-d6): δ 1.42-1.45 (m, 2H), 1.54-1.56 (m, 2H), 8.48-8.53 (m, 2H), 8.86-8.87 (d, 1H, J=1.6 Hz), 12.58 (s, 1H). LCMS: (ES+) m/z=165.2 (M+H)+

後処理

  1. temperaturecooled to room temperature
  2. filtrationThe mixture was filtered through a pad of celite with MeOH
  3. washwash
  4. concentrationthe filtrate was concentrated
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-8498f98deac24f88b1805d0deab2fa3b
出典データセット
uspto-grants-2011_08
特許番号
US07994171B2

反応ノート

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