Methanol → Methyl 2-aminopyridine-4-carboxylate

HRID 1355504

반응식

HRID 1355504 반응식
C([NH:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][N:13]=1)[C:8]([OH:10])=[O:9])(=O)C.[CH3:14]O>>[CH3:14][O:10][C:8](=[O:9])[C:7]1[CH:11]=[CH:12][N:13]=[C:5]([NH2:4])[CH:6]=1

참가 물질

3

반응물 2

HCID 887MethanolHCID 37744662-Acetamidopyridine-4-carboxylic acid

생성물 1

HCID 236984Methyl 2-aminopyridine-4-carboxylate

실험 절차

2-Acetylamino-isonicotinic acid (3.10 g, 17.2 mmol) was stirred in 35 mL MeOH at 0° C. HCl (g) was bubbled through the solution for 10 min and then the reaction was heated to reflux. After 16 h the reaction was concentrated in vacuo. The residue was diluted with water and the pH was adjusted to 7 with Na2CO3 (s). A white precipitate formed which was filtered to afford a portion of pure desired product. The aqueous phase was extracted three time with 95:5 DCM/nBuOH. The organic phases were dried over Na2SO4, filtered and concentrated to afford more of the pure desired product as a white solid. 1H NMR (CDCl3) δ 8.19 (d, 1H, J=5.3 Hz), 7.17 (dd, 1H, J=1.4, 5.3 Hz), 7.07 (d, 1H, J=1.3 Hz), 4.64 (bs, 2H), 3.92 (s, 3H). MS [M+H]+=153.0.

후처리

  1. customHCl (g) was bubbled through the solution for 10 min
  2. temperaturethe reaction was heated to reflux
  3. concentrationAfter 16 h the reaction was concentrated in vacuo
  4. additionThe residue was diluted with water
  5. customA white precipitate formed which
  6. filtrationwas filtered

출처 및 근거

ORD 기록
ord-dde182351e7c40b08bbf2b42235e6de9
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06586424B2

연결된 노트

불러오는 중…