Triethylamine → 3-Methoxypyridine-2-carbonitrile

HRID 723709

반응식

HRID 723709 반응식
[CH3:1][O:2][C:3]1[CH:4]=[N+:5]([O-])[CH:6]=[CH:7][CH:8]=1.[CH2:10]([N:12](CC)CC)C>C(#N)C>[C:10]([C:4]1[C:3]([O:2][CH3:1])=[CH:8][CH:7]=[CH:6][N:5]=1)#[N:12]

참가 물질

4

반응물 2

HCID 8471TriethylamineHCID 139850Pyridine, 3-methoxy-, 1-oxide

생성물 1

HCID 113324933-Methoxypyridine-2-carbonitrile

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

3-Methoxypyridine-1-oxide (25.2g, 209 mmol) was dissolved in acetonitrile (260 mL). Trimethylsilycyanide (66.35g, 669 mmol) and triethylamine (45.13g, 446 mmol) were added and the reaction mixture heated at reflux for overnight. The cooled solution was concentrated in vacuo to give a brown solid which was partitioned between CH2Cl2 and 3M Na2CO3. The organic layer was separated, washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by silica gel chomatography using 1:1 EtOAc/hexanes as eluent. Compound 762B was isolated (17.63g, 63%) as a light yellow solid. HPLC: 96.2% at 1,37 min(YMC S5 ODS column) eluting with 10–90% aqueous methanol containing 0.2% phosphoric acid over a 4 min gradient monitoring at 220 nm. MS (ES): m/z 134.88 [M+H]+.

후처리

  1. temperaturethe reaction mixture heated
  2. temperatureat reflux for overnight
  3. concentrationThe cooled solution was concentrated in vacuo
  4. customto give a brown solid which
  5. customwas partitioned between CH2Cl2 and 3M Na2CO3
  6. customThe organic layer was separated
  7. washwashed with brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by silica gel chomatography

출처 및 근거

ORD 기록
ord-a44a7e905c3945129bac12312612791d
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07141578B2

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