Methanol → Methyl 2-chloro-6-methyl-5-nitronicotinate
Reaction equation
[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]Participants
6
Conditions
- Temperature
- 133 °C
Procedure
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;
Workup
- temperatureAfter cooling to RT
- concentrationthe mixture was concentrated in vacuo
- temperatureThe residue was cooled in an ice bath
- concentrationThe mixture was concentrated in vacuo
- customthe residue was partitioned between water (300 ml) and EtOAc (300 ml)
- dry with materialThe organics were dried (MgSO4)
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-1ccaf4b91396451a842f27282555ccd9
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09073921B2
Reaction notes
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