Ammonium formate → Methyl 5-amino-6-methylnicotinate

HRID 335312노트

반응식

HRID 335312 반응식
Cl[C:2]1[N:11]=[C:10]([CH3:12])[C:9]([N+:13]([O-])=O)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C([O-])=O.[NH4+]>CO>[NH2:13][C:9]1[C:10]([CH3:12])=[N:11][CH:2]=[C:3]([CH:8]=1)[C:4]([O:6][CH3:7])=[O:5]

참가 물질

4

반응물 2

HCID 2723923Ammonium formateHCID 86672545Methyl 2-chloro-6-methyl-5-nitronicotinate

생성물 1

HCID 58662456Methyl 5-amino-6-methylnicotinate

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Methyl 2-chloro-6-methyl-5-nitronicotinate (step 1) (6.9 g, 29.9 mmol) was added to a suspension of ammonium formate (18.87 g, 299 mmol) and 10% Pd(Carbon) (0.522 g, 0.491 mmol) in MeOH (330 ml) and the mixture was heated at reflux for 3 hrs. After cooling to RT, the mixture was filtered through Celite® (filter material) and washed through with MeOH. The solvent was removed in vacuo and the crude product was triturated with EtOAc to give an orange solid. Purification by chromatography on silica eluting with 0-100% EtOAc in iso-hexane afforded the title product.

후처리

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 3 hrs
  3. filtrationthe mixture was filtered through Celite® (filter material)
  4. washwashed through with MeOH
  5. customThe solvent was removed in vacuo
  6. customthe crude product was triturated with EtOAc
  7. customto give an orange solid
  8. customPurification by chromatography on silica eluting with 0-100% EtOAc in iso-hexane

출처 및 근거

ORD 기록
ord-46e6da5b281d4b7aaa696135f0584238
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883819B2

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