HCID 21875453、化合物 → 5-Amino-3-methoxypyridine-2-carbonitrile

HRID 2110472ノート

反応式

HRID 2110472 の反応式
[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

参加物

4

反応物 1

HCID 21875453HCID 21875453、化合物

生成物 1

HCID 218753365-Amino-3-methoxypyridine-2-carbonitrile収率 97%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 22609514Ethyl acetate acetate溶媒

反応条件

温度
65 °C

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-e1a854ecaea64442ae3db4655ae50544
出典データセット
uspto-grants-2009_04
特許番号
US07517904B2

反応ノート

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