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

HRID 14195

반응식

HRID 14195 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

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) δ 7.62, 7.46, 4.44, 3.41, 3.33, 1.60, 1.41, 0.98.

후처리

  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

출처 및 근거

ORD 기록
ord-364ef14840254a0683460e5688d6b9ba
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07727997B2

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