Hydrochloric Acid → Methyl 4-butyl-8-cyano-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate

HRID 348984

반응식

HRID 348984 반응식
Br[C:2]1[C:11]2[O:10][CH2:9][CH2:8][N:7]([CH2:12][CH2:13][CH2:14][CH3:15])[C:6]=2[CH:5]=[C:4]([C:16]([O:18][CH3:19])=[O:17])[CH:3]=1.[Cu](C#N)[C:21]#[N:22].Cl>CN1C(=O)CCC1>[CH2:12]([N:7]1[C:6]2[CH:5]=[C:4]([C:16]([O:18][CH3:19])=[O:17])[CH:3]=[C:2]([C:21]#[N:22])[C:11]=2[O:10][CH2:9][CH2:8]1)[CH2:13][CH2:14][CH3:15]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 21086218Methyl 8-bromo-4-butyl-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylateHCID 178418260HCID 178418260, 화합물

생성물 1

HCID 21086202Methyl 4-butyl-8-cyano-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate수율 66.7%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
175 °C

실험 절차

To a flask containing methyl 8-bromo-4-butyl-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate (0.33 g) was added NMP (7 mL), followed by copper cyanide (0.18 g). The mixture was then heated to 175° C. and stirred overnight. The resulting mixture was cooled to room temperature and poured into 1 N hydrochloric acid. The acidic aqueous layer was extracted with ethyl acetate, washed with 1 N hydrochloric acid (15 mL), saturated sodium bicarbonate (15 mL), and brine, dried (magnesium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 1:9 ethyl acetate/hexanes) provided 184 mg of the title compound: 1H NMR (300 MHz, CDCl3) δ 7.55, 7.43, 4.41, 3.89, 3.39, 3.31, 1.58, 1.40, 0.97.

후처리

  1. temperatureThe resulting mixture was cooled to room temperature
  2. extractionThe acidic aqueous layer was extracted with ethyl acetate
  3. washwashed with 1 N hydrochloric acid (15 mL), saturated sodium bicarbonate (15 mL), and brine
  4. dry with materialdried (magnesium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by flash column chromatography (silica, 1:9 ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-36cb40f78eb54995aca347f0d29dc574
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07176242B2

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