Water → Quinolin-3-ylmethanamine

HRID 1271776노트

반응식

HRID 1271776 반응식
[N:1]([CH2:4][C:5]1[CH:6]=[N:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1COCC1>[NH2:1][CH2:4][C:5]1[CH:6]=[N:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2

참가 물질

5

반응물 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 18400510HCID 18400510, 화합물

생성물 1

HCID 6483745Quinolin-3-ylmethanamine수율 48.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

3(azidomethyl)quinoline (250 mg, 1.36 mmol) and triphenylphosphine (880 mg, 3.36 mmol, 2.5 equiv) were dissolved in 10 mL THF. The reaction mixture was treated with 0.5 mL of H2O and refluxed for 6 hours. The reaction mixture was cooled and partitioned between Et2O and 1N HCl. The aqueous portion was then treated with 1N NaOH until basic and extracted into EtOAc. The organic portion was dried over Na2SO4 and concentrated under reduced pressure to give the title compound (104 mg) as a brown oil. MS(CI) m/e 159 (M+H)+.

후처리

  1. temperaturerefluxed for 6 hours
  2. temperatureThe reaction mixture was cooled
  3. custompartitioned between Et2O and 1N HCl
  4. additionThe aqueous portion was then treated with 1N NaOH until basic and
  5. extractionextracted into EtOAc
  6. dry with materialThe organic portion was dried over Na2SO4
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-dd52068fedcd4c14a227c6f2b6d00c1d
출처 데이터셋
uspto-grants-2007_04
특허 번호
USRE039591E1

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