HCID 21875453, 화합물 → 5-Amino-3-methoxypyridine-2-carbonitrile

HRID 2378454노트

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HRID 2378454 반응식
[C:1]([C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([N+:11]([O-])=O)=[CH:5][N:4]=1)#[N:2]>CCOC(C)=O.CC(O)=O.[Fe]>[NH2:11][C:6]1[CH:7]=[C:8]([O:9][CH3:10])[C:3]([C:1]#[N:2])=[N:4][CH:5]=1

참가 물질

4

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HCID 21875453HCID 21875453, 화합물

생성물 1

HCID 218753365-Amino-3-methoxypyridine-2-carbonitrile수율 97%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 22609514Ethyl acetate acetate용매

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온도
65 °C

실험 절차

2-Cyano-3-methoxy-5-nitropyridine (1.0 g, 5.6 mmol) was dissolved in 1:1 EtOAc/AcOH (10 mL) and heated to 65° C. Iron powder (1.61 g, 28 mmol, 325 mesh) was added and the mixture stirred for two h. The mixture was filtered though Celite and the filtrate concentrated in vacuo. The residue was partitioned between EtOAc and saturated aqueous sodium bicarbonate. The organic layer was separated, washed with brine, dried (MgSO4), filtered and concentrated. The residue was purified by SiO2 Prep-TLC using CH2Cl2 as the eluent to give the compound 762D (0.805 g, 97%) as an off-white solid. HPLC: 100% at 1.31 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 149.90 [M+H]+.

후처리

  1. filtrationThe mixture was filtered though Celite
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe residue was partitioned between EtOAc and saturated aqueous sodium bicarbonate
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by SiO2 Prep-TLC

출처 및 근거

ORD 기록
ord-cc8e27b55f35400d8996dcc6a6d39e4f
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07470797B2

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