Potassium Hydroxide → 4-Butyl-8-cyano-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylic acid

HRID 348985

反応式

HRID 348985 の反応式
[CH2:1]([N:5]1[C:10]2[CH:11]=[C:12]([C:17]([O:19]C)=[O:18])[CH:13]=[C:14]([C:15]#[N:16])[C:9]=2[O:8][CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4].[OH-].[K+]>CO.O>[CH2:1]([N:5]1[C:10]2[CH:11]=[C:12]([C:17]([OH:19])=[O:18])[CH:13]=[C:14]([C:15]#[N:16])[C:9]=2[O:8][CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4]

参加物

5

反応物 2

HCID 14797Potassium HydroxideHCID 21086202Methyl 4-butyl-8-cyano-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate

生成物 1

HCID 210859314-Butyl-8-cyano-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylic acid収率 88.2%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

To a stirred solution of Methyl 4-butyl-8-cyano-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate (184 mg) in methanol (3 mL) was added potassium hydroxide (7 mL of a 1.0 M solution in water). The mixture was stirred at room temperature overnight then concentrated under reduced pressure. The residue was diluted with water and washed with ethyl acetate. The aqueous layer was acidified to pH 4 with 1 N hydrochloric acid and extracted with chloroform (4×100 mL). The combined organic extracts were dried (sodium sulfate), filtered, and concentrated under reduced pressure to give 154 mg of the title compound: 1H NMR (300 MHz, CDCl3) (57.62, 7.46, 4.44, 3.41, 3.33, 1.60, 1.41, 0.98.

後処理

  1. concentrationthen concentrated under reduced pressure
  2. additionThe residue was diluted with water
  3. washwashed with ethyl acetate
  4. extractionextracted with chloroform (4×100 mL)
  5. dry with materialThe combined organic extracts were dried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-a6f17698ccba43aaa558f4226778b18a
出典データセット
uspto-grants-2007_02
特許番号
US07176242B2

関連ノート

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