Methanol → Methyl 2-chloro-6-methyl-5-nitronicotinate

HRID 1521341노트

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HRID 1521341 반응식
[CH3:1][C:2]1[NH:7][C:6](=O)[C:5](C(O)=O)=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].CN([CH:18]=[O:19])C.O=P(Cl)(Cl)[Cl:22].[CH3:25][OH:26]>ClC1C=CC=CC=1>[Cl:22][C:6]1[N:7]=[C:2]([CH3:1])[C:3]([N+:12]([O-:14])=[O:13])=[CH:4][C:5]=1[C:25]([O:19][CH3:18])=[O:26]

참가 물질

6

반응물 4

HCID 887MethanolHCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 263703636-Methyl-5-nitro-2-oxo-1,2-dihydropyridine-3-carboxylic acid

생성물 1

HCID 86672545Methyl 2-chloro-6-methyl-5-nitronicotinate

시약·촉매·용매 1

HCID 7964Chlorobenzene용매

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온도
133 °C

실험 절차

To a suspension of 6-methyl-5-nitro-2-oxo-1,2-dihydropyridine-3-carboxylic acid (commercially available) (12.5 g, 63.1 mmol) in chlorobenzene (210 ml) was added DMF (2.442 ml, 31.5 mmol) followed by POCl3 (23.52 ml, 252 mmol). The mixture was heated at 133° C. for 1 hr. After cooling to RT, the mixture was concentrated in vacuo. The residue was cooled in an ice bath, treated with MeOH (200 ml, 4944 mmol) and stirred at RT for 16 hrs. The mixture was concentrated in vacuo and the residue was partitioned between water (300 ml) and EtOAc (300 ml). The organics were dried (MgSO4) and concentrated in vacuo to afford the title compound as a red crystalline solid;

후처리

  1. temperatureAfter cooling to RT
  2. concentrationthe mixture was concentrated in vacuo
  3. temperatureThe residue was cooled in an ice bath
  4. concentrationThe mixture was concentrated in vacuo
  5. customthe residue was partitioned between water (300 ml) and EtOAc (300 ml)
  6. dry with materialThe organics were dried (MgSO4)
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-1ccaf4b91396451a842f27282555ccd9
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073921B2

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