4-Methoxybenzylamine → HCID 23856703, 화합물

HRID 901236노트

반응식

HRID 901236 반응식
[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

참가 물질

4

반응물 2

HCID 754524-MethoxybenzylamineHCID 762582-Chloronicotinic acid

생성물 1

HCID 23856703HCID 23856703, 화합물수율 77.2%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f395fbfa563143b4be4d79e1b0baa0e0
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07361760B2

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