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

HRID 564495

反応式

HRID 564495 の反応式
[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]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 6331Borane3 回HCID 8028Tetrahydrofuran5 回HCID 7360493-Bromo-4-methoxybenzonitrile

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
50 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-49cc177301fa4a26926a7c90e5ac8efe
出典データセット
uspto-grants-2011_11
特許番号
US08067408B2

関連ノート

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