4-Methoxybenzylamine → HCID 23856703、化合物

HRID 901236ノート

反応式

HRID 901236 の反応式
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1.Cl[C:12]1[N:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14]([OH:16])=[O:15]>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH:8][C:12]2[N:20]=[CH:19][CH:18]=[CH:17][C:13]=2[C:14]([OH:16])=[O:15])=[CH:5][CH:4]=1

参加物

4

反応物 2

HCID 754524-MethoxybenzylamineHCID 762582-Chloronicotinic acid

生成物 1

HCID 23856703HCID 23856703、化合物収率 77.2%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

p-Methoxybenzylamine (8.24 mL, 63.5 mmol) was added to a solution of 2-chloronicotinic acid (5 g, 31.7 mmol) in pyridine and refluxed overnight. The pyridine was distilled and the residue was dissolved in 1N NaOH. The solution was diluted with water to adjust the pH to 10 to 11 and washed by dichloromethane. The aqueous phase was neutralized with cold aqueous 10% HCl solution to adjust the pH to 4 to 5. The solids formed were filtered, washed with cold water, and dried in a vacuum oven to yield 6.32 g (77%) of 2-(4-methoxy-benzylamino)-nicotinic acid (11) as white solids. MP: 229° C.; 1H-NMR (DMSO-d6): δ 3.72 (s, 3H), 4.60 (d, J=3.6 Hz, 2H), 6.40 (dd, J=4.9, 7.7 Hz, 1H), 6.62 (d, J=7.6 Hz, 2H), 7.25 (d, J=7.6 Hz, 2H), 8.09 (dd, J=1.8, 7.0 Hz, 1H), 8.26 (dd, J=1.8, 7.0 Hz, 1H), 8.48 (br. s, 1H), 13.11 (s, 1H); EIMS: 259 (M+1), 281 (M+23).

後処理

  1. temperaturerefluxed overnight
  2. distillationThe pyridine was distilled
  3. dissolutionthe residue was dissolved in 1N NaOH
  4. additionThe solution was diluted with water
  5. washwashed by dichloromethane
  6. customThe solids formed
  7. filtrationwere filtered
  8. washwashed with cold water
  9. customdried in a vacuum oven

出典と根拠

ORDレコード
ord-f395fbfa563143b4be4d79e1b0baa0e0
出典データセット
uspto-grants-2008_04
特許番号
US07361760B2

反応ノート

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