3-Pyridinecarboxaldehyde → 3-[(Pyridin-3-ylmethyl)-amino]-phthalic acid dimethyl ester

HRID 906797

反応式

HRID 906797 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=O)[CH:2]=1.[CH3:9][O:10][C:11](=[O:28])[C:12]1[C:13](=[C:18]([NH:22]CCCCC)[CH:19]=[CH:20][CH:21]=1)[C:14]([O:16][CH3:17])=[O:15]>C(OCC)C>[CH3:9][O:10][C:11](=[O:28])[C:12]1[C:13](=[C:18]([NH:22][CH2:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[CH:19]=[CH:20][CH:21]=1)[C:14]([O:16][CH3:17])=[O:15]

参加物

4

反応物 2

HCID 103713-PyridinecarboxaldehydeHCID 210401313-Pentylamino-phthalic acid dimethyl ester

生成物 1

HCID 210401363-[(Pyridin-3-ylmethyl)-amino]-phthalic acid dimethyl ester収率 61%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

3-Pyridinecarboxaldehyde (0.94 ml, 10 mmol) was treated in the same manner as described above for the synthesis of 3-pentylamino-phthalic acid dimethyl ester. After removal of pyridine the residue was dissolved in methylene chloride (100 ml) and washed with water (2×100 ml), saturated NaHCO3 (2×100 ml), brine (1×100 ml), dried (magnesium sulfate), and filtered. The solvent was evaporated in vacuo to give an oil. The oil was dissolved in diethyl ether (100 ml) and extracted with 0.1 N HCl (2×100 ml). The combined aqueous HCl extracts were washed with diethyl ether (2×100 ml) and the pH adjusted to 10 by dropwise addition of saturated Na2CO3. The product was extracted with diethyl ether (3×100 ml). The combined ether extracts were washed with brine (1×100 ml), dried (magnesium sulfate), and filtered. The solvent was evaporated in vacuo to give 0.91 g (61%) of product as a light yellow oil which was used without further purification: 1H NMR (CDCl3) δ 8.61 (d, J=2.0 Hz, 1H), 8.53 (dd, J=1.1 Hz and 4.8 Hz, 1H), 7.65 (d, J=7.9 Hz, 1H), 7.31-7.21 (m, 3H), 6.85 (d, J=7.3 Hz, 1H), 6.69 (d, J=8.5 Hz, 1H), 4.45 (d, J=5.7 Hz, 2H), 3.87 (s, 3H), 3.85 (s, 3H).

後処理

  1. customAfter removal of pyridine the residue
  2. dissolutionwas dissolved in methylene chloride (100 ml)
  3. washwashed with water (2×100 ml), saturated NaHCO3 (2×100 ml), brine (1×100 ml)
  4. dry with materialdried (magnesium sulfate)
  5. filtrationfiltered
  6. customThe solvent was evaporated in vacuo
  7. customto give an oil
  8. extractionextracted with 0.1 N HCl (2×100 ml)
  9. washThe combined aqueous HCl extracts were washed with diethyl ether (2×100 ml)
  10. additionthe pH adjusted to 10 by dropwise addition of saturated Na2CO3
  11. extractionThe product was extracted with diethyl ether (3×100 ml)
  12. washThe combined ether extracts were washed with brine (1×100 ml)
  13. dry with materialdried (magnesium sulfate)
  14. filtrationfiltered
  15. customThe solvent was evaporated in vacuo

出典と根拠

ORDレコード
ord-4a287f0881814039bec21295d9082d4a
出典データセット
uspto-grants-2011_09
特許番号
US08012997B2

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