Ammonium formate → Methyl 5-amino-6-methylnicotinate

HRID 1521342노트

반응식

HRID 1521342 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.[Pd]>[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

5

반응물 2

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

생성물 1

HCID 58662456Methyl 5-amino-6-methylnicotinate

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 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-7f938c882d7e43b0b1924b2432e31fa5
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073921B2

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