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

HRID 335311ノート

反応式

HRID 335311 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 7964Chlorobenzene溶媒

反応条件

温度
133 °C

実験手順

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;

後処理

  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

出典と根拠

ORDレコード
ord-75341a59a63744ffb22adc8ec73f879c
出典データセット
uspto-grants-2014_11
特許番号
US08883819B2

反応ノート

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