Water → Methyl 6-chloro-4-cyano-2-(m-tolylamino)nicotinate

HRID 515974ノート

反応式

HRID 515974 の反応式
Cl[C:2]1[N:11]=[C:10]([Cl:12])[CH:9]=[C:8]([C:13]#[N:14])[C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(N(CC)CC)C.[NH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[CH:24]=1.O>C1COCC1>[Cl:12][C:10]1[CH:9]=[C:8]([C:13]#[N:14])[C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([NH:22][C:23]2[CH:24]=[C:25]([CH3:29])[CH:26]=[CH:27][CH:28]=2)[N:11]=1

参加物

6

反応物 4

HCID 962WaterHCID 7934m-ToluidineHCID 8471TriethylamineHCID 58317683Methyl 2,6-dichloro-4-cyanonicotinate

生成物 1

HCID 58317587Methyl 6-chloro-4-cyano-2-(m-tolylamino)nicotinate収率 33.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of methyl 2,6-dichloro-4-cyanonicotinate (455 mg, 1.97 mmol), triethylamine (0.549 mL, 3.94 mmol) and m-toluidine (0.32 mL, 2.95 mmol) in THF (10 mL) was stirred at RT for 3 days. Water was added to the resulting mixture, and the aqueous phase was extracted with EtOAc. The organic phases were combined, washed with H2O and brine, dried over MgSO4, and evaporated. The residue was purified by chromatography on SiO2 to give the title compound as a yellow solid (198 mg, 33.3%). 1H NMR (500 MHz, CDCl3) δ ppm 2.40 (s, 3 H), 3.99 (s, 3H), 6.92 (s, 1H), 7.05-7.14 (m, 4H), 7.33 (t, J=7.81 Hz, 1H).

後処理

  1. extractionthe aqueous phase was extracted with EtOAc
  2. washwashed with H2O and brine
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customThe residue was purified by chromatography on SiO2

出典と根拠

ORDレコード
ord-4eddae5bd05c4b7494c637f5503548b4
出典データセット
uspto-grants-2015_08
特許番号
US09108970B2

反応ノート

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