Ammonium formate → Methyl 5-amino-6-methylnicotinate

HRID 1521342ノート

反応式

HRID 1521342 の反応式
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]

参加物

5

反応物 2

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

生成物 1

HCID 58662456Methyl 5-amino-6-methylnicotinate

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7f938c882d7e43b0b1924b2432e31fa5
出典データセット
uspto-grants-2015_07
特許番号
US09073921B2

反応ノート

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