Hydrochloric Acid → (3-Bromo-4-methoxyphenyl)methanamine

HRID 564495

반응식

HRID 564495 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[C:5]#[N:6].C1COCC1.B.Cl>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH2:5][NH2:6])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 6331Borane3회HCID 8028Tetrahydrofuran5회HCID 7360493-Bromo-4-methoxybenzonitrile

생성물 1

HCID 22026276(3-Bromo-4-methoxyphenyl)methanamine

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
50 °C

실험 절차

3-Bromo-4-(methyloxy)benzonitrile (2.12 g, 10 mmol), THF (30 mL), and 1.5 M borane in THF (30 mL, 45 mmols) were combined and stirred under argon at reflux. The additional 1.5 M borane in THF (30 mL, 45 mmols) and reflux continued. THF (30 mL), and 1.5 M borane in THF (30 mL, 45 mmols) was again added and the mixture refluxed for a total of ten days to drive the reaction to completion. The reaction was worked up by the cautious addition of ethanol followed by 1N HCl until the pH was 2. This mixture was then heated to 50° C. for 4 h. The solvents were pumped off, and the residue partitioned between EtOAc and water. The aqueous phase was washed 3× with EtOAc and adjusted to pH 10 by the addition of 2.5 N NaOH. The aqueous phase was extracted 3× with EtOAc. The combined organic phases were dried over anhydrous Na2SO4, filtered and concentrated to give the title compound. LC-MS m/z 198.7 (M−NH2), 0.99 min (ret time).

후처리

  1. temperatureat reflux
  2. temperaturethe mixture refluxed for a total of ten days
  3. customthe reaction to completion
  4. customthe residue partitioned between EtOAc and water
  5. washThe aqueous phase was washed 3× with EtOAc
  6. additionadjusted to pH 10 by the addition of 2.5 N NaOH
  7. extractionThe aqueous phase was extracted 3× with EtOAc
  8. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated

출처 및 근거

ORD 기록
ord-49cc177301fa4a26926a7c90e5ac8efe
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08067408B2

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