Water → HCID 67328647、化合物

HRID 1846164ノート

反応式

HRID 1846164 の反応式
[CH3:1][N:2]([CH3:16])[C:3]1[CH:12]=[C:11]([O:13][CH3:14])[C:6](C(OC)=O)=[C:5]([CH3:15])[N:4]=1.O>Cl>[CH3:14][O:13][C:11]1[CH:6]=[C:5]([CH3:15])[N:4]=[C:3]([N:2]([CH3:16])[CH3:1])[CH:12]=1

参加物

4

反応物 2

HCID 962WaterHCID 67328722HCID 67328722、化合物

生成物 1

HCID 67328647HCID 67328647、化合物

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒

実験手順

A solution containing 340 mg (1.52 mmol) of methyl 6-(Dimethylamino)-4-methoxy-2-methylnicotinate in 5 mL of 6N aq. HCl was stirred at reflux for 16 h. The reaction mixture was poured into 50 mL of water and the pH was set up to 12. The mixture was extracted with two 40-mL portions of ethyl acetate. The combined organic solution was washed with a 40-mL portion of brine, dried (MgSO4) and concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column (2×6 cm). Elution with 9:1 dichloromethane-methanol afforded the expected product as a colorless oil: yield 87 mg (34%); silica gel TLC Rf 0.25 (9:1 dichloromethane-methanol); 1H NMR (CDCl3) δ 2.33 (s, 3H), 3.02 (s, 6H), 3.75 (s, 3H), 5.77 (s, 1H) and 6.03 (s, 1H); 13C NMR (CDCl3) δ 24.8, 38.0, 38.0, 54.7, 87.4, 98.5, 157.9, 160.8, 167.5; mass spectrum (APCI), m/z 167.1183 (M+H)+ (C9H15N2O requires 167.1184).

後処理

  1. temperatureat reflux for 16 h
  2. extractionThe mixture was extracted with two 40-mL portions of ethyl acetate
  3. washThe combined organic solution was washed with a 40-mL portion of brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under diminished pressure
  6. customThe residue was purified by chromatography on a silica gel column (2×6 cm)
  7. washElution with 9:1 dichloromethane-methanol

出典と根拠

ORDレコード
ord-47000ce11149437f8e52c2f6f6328d2f
出典データセット
uspto-grants-2015_02
特許番号
US08952025B2

反応ノート

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